Ashland Rentals

Close

Enter dates for more accurate prices

Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more

184 Houses

    30

    Affordable Windham Getaway (near private creek!)

    New York / Ashland

    Ashland house

    3 7 2 nights min

    • 3 bedrooms
    • sleeps 7
    • 2 nights min
    • Child Friendly
    • Air conditioning
    • Private garden

    Price per night from

    $144

    Price per night from

    $144

    Great rentals within 20 miles that match your search

    Distance approx 5.66 km from Ashland Show on Map

    (37) Excellent 

    Certificate of Excellence

      24

      *4SeasonNirvana*Hot Tub, WiFi, Fire Pit, Fireplace, 2 WEBERs, Wndhm Mtn Vw

      Catskill Region / Windham

      Windham house

      4 8 min stay varies

      • 4 bedrooms
      • sleeps 8
      • min stay varies
      • Nearest beach 29 mi
      • Child Friendly
      • Air conditioning
      “Terrific Rental in Windham” This is a great rental property. The house is very well maintained and comes complete with everything you need for your visit. This includes the kitchen where many other rental properties offer sparse and/or low quality ut

      Certificate of Excellence

      Price per night from

      $200

      Responds fast!
      avg. 31 minutes

      Price per night from

      $200

      Distance approx 4.07 km from Ashland Show on Map

      (1) Excellent 

        14

        Beautiful apartment with great views!

        Catskill Region / Windham

        Windham apartment

        2 4 2 nights min

        • 2 bedrooms
        • sleeps 4
        • 2 nights min
        • Child Friendly
        • Private garden

        Price per night from

        $228

        Responds fast!
        avg. 3 hours 22 minutes

        Price per night from

        $228

        Distance approx 12.87 km from Ashland

          32

          Private home on secluded estate near Hunter Mt, NY

          Catskill Region / Hunter

          Hunter house

          2 6 2 nights min

          • 2 bedrooms
          • sleeps 6
          • 2 nights min
          • Child Friendly

          Price per night from

          $342

          Price per night from

          $342

          Distance approx 18.16 km from Ashland

            24

            Quiet Mt. Tremper/Catskills Cottage Near Woodstock

            New York / Mount Tremper

            Mount Tremper cottage

            2 4 min stay varies

            • 2 bedrooms
            • sleeps 4
            • min stay varies
            • Ski
            • Child Friendly

            Price per night from

            $171

            Responds fast!
            avg. 24 minutes

            Price per night from

            $171

            Distance approx 10.53 km from Ashland

              25

              Cozy Home w/Hot Tub - 1.6 Miles to Hunter Mountain

              Catskill Region / Hunter

              Hunter house

              6 10 min stay varies

              • 6 bedrooms
              • sleeps 10
              • min stay varies
              • Ski
              • Child Friendly

              Price per night from

              $542

              Responds fast!
              avg. 24 minutes

              Price per night from

              $542

              Distance approx 10.62 km from Ashland

              (7) Excellent 

                11

                Cozy Log Cabin

                Catskill Region / Durham

                Durham log cabin

                2 6 2 nights min

                • 2 bedrooms
                • sleeps 6
                • 2 nights min
                • Child Friendly
                • Ask about pets
                • Private garden

                Price per night from

                $223

                Responds fast!
                avg. 2 hours 6 minutes

                Price per night from

                $223

                Distance approx 15.53 km from Ashland

                (2) Excellent 

                  6

                  LAKE FRONT NYC DESIGNER Cabin - CATSKILLS, NY.

                  Catskill Region / Stamford

                  Stamford log cabin

                  3 7 2 nights min

                  • 3 bedrooms
                  • sleeps 7
                  • 2 nights min
                  • Child Friendly
                  • Private garden

                  Price per night from

                  $342

                  Responds fast!
                  avg. 2 hours 32 minutes

                  Price per night from

                  $342

                  Distance approx 16.25 km from Ashland

                  (1) Excellent 

                    20

                    Hamilton at the Kaaterskill House

                    Catskill Region / Stamford

                    Stamford room

                    1 2 1 night min

                    • 1 bedroom
                    • sleeps 2
                    • 1 night min
                    • Child Friendly

                    Price per night from

                    $63

                    Price per night from

                    $63

                    Distance approx 11.82 km from Ashland

                    (5) Excellent 

                      25

                      Catskill Mountain View House, Belleayre, Fire Pit!

                      Catskill Region / Roxbury

                      Roxbury house

                      4 9 2 nights min

                      • 4 bedrooms
                      • sleeps 9
                      • 2 nights min
                      • Nearest beach 13 mi
                      • Ski
                      • Child Friendly
                      “Best house ever” The house is in a beautiful setting. So many things to do in the area from antique shopping, golf in the summer, winter skiing, hiking, really great restaurants. Once you've seen the house though, you won't want to leave. Great layout

                      Price per night from

                      $434

                      Price per night from

                      $434

                      Distance approx 8.46 km from Ashland

                        24

                        NEW! 5BR House 1 Mile to Hunter Mountain Chairlift

                        Catskill Region / Hunter

                        Hunter house

                        5 16 2 nights min

                        • 5 bedrooms
                        • sleeps 16
                        • 2 nights min
                        • Ski
                        • Child Friendly
                        • Pet Friendly

                        Price per night from

                        $684

                        Responds fast!
                        avg. 34 minutes

                        Price per night from

                        $684

                        Distance approx 8.17 km from Ashland

                          13

                          SIX BEDROOMS SIX BATHS

                          Catskill Region / Hunter

                          Hunter house

                          6 24 2 nights min

                          • 6 bedrooms
                          • sleeps 24
                          • 2 nights min
                          • Child Friendly
                          • Pet Friendly
                          • Private garden

                          Price per night from

                          $570

                          Price per night from

                          $570

                          Distance approx 18.03 km from Ashland

                          (22) Excellent 

                            18

                            Country Farmhouse along the Catskill Scenic Trail

                            Catskill Region / Hobart

                            Hobart house

                            3 6 min stay varies

                            • 3 bedrooms
                            • sleeps 6
                            • min stay varies
                            • Child Friendly
                            • Pet Friendly
                            “Peaceful” Had a great time. The owners of the farm are warm and thoughtful people. Clean,beautiful farm setting and well equipped home . The only thing that would've made it more perfect would be air conditioning. It did cool down nicely at night b

                            Price per night from

                            $171

                            Price per night from

                            $171

                            Distance approx 17.89 km from Ashland

                              4

                              Second Wind

                              Catskill Region / Hobart

                              Hobart apartment

                              2 6 1 night min

                              • 2 bedrooms
                              • sleeps 6
                              • 1 night min
                              • Child Friendly
                              • Air conditioning
                              • Private garden

                              Price per night from

                              $143

                              Price per night from

                              $143

                              Distance approx 5.02 km from Ashland Show on Map

                              (5) Excellent 

                                18

                                Mountain House Retreat

                                Catskill Region / Windham

                                Windham house

                                5 10 2 nights min

                                • 5 bedrooms
                                • sleeps 10
                                • 2 nights min
                                • Child Friendly
                                • Pet Friendly
                                • Private garden
                                “Beautiful! Relaxing! Perfect!” I spent 4th of July weekend with a group of friends at this wonderful mountain retreat, and it was all that we wished and more!! The views are spectacular, the private pond and the mountains added so much to our stay.

                                Price per night from

                                $342

                                Price per night from

                                $342

                                Distance approx 18.41 km from Ashland

                                  9

                                  Catskill Mtn.views Horses/ Margaretville/Roxbury

                                  Catskill Region / Margaretville

                                  Margaretville house

                                  2 5 2 nights min

                                  • 2 bedrooms
                                  • sleeps 5
                                  • 2 nights min
                                  • Child Friendly
                                  • Private garden

                                  Price per night from

                                  $227

                                  Price per night from

                                  $227

                                  Distance approx 14.75 km from Ashland

                                  (2) Excellent 

                                    14

                                    Midcentury Modern in the Woods

                                    Catskill Region / Shandaken

                                    Shandaken house

                                    2 5 2 nights min

                                    • 2 bedrooms
                                    • sleeps 5
                                    • 2 nights min
                                    • Child Friendly
                                    • Ask about pets
                                    • Private garden

                                    Price per night from

                                    $200

                                    Price per night from

                                    $200

                                    Distance approx 3.35 km from Ashland Show on Map

                                      9

                                      Windham Mountain Ski House

                                      Catskill Region / Windham

                                      Windham house

                                      5 10 90 nights min

                                      • 5 bedrooms
                                      • sleeps 10
                                      • 90 nights min
                                      • Child Friendly
                                      • Private garden

                                      Price per night from

                                      $570

                                      Price per night from

                                      $570

                                      Distance approx 16.16 km from Ashland

                                      (5) Excellent 

                                        7

                                        Cottage in the country

                                        Catskill Region / Phoenicia

                                        Phoenicia log cabin

                                        2 4 2 nights min

                                        • 2 bedrooms
                                        • sleeps 4
                                        • 2 nights min
                                        • Child Friendly
                                        • Ask about pets

                                        Price per night from

                                        $171

                                        Price per night from

                                        $171

                                        Distance approx 5.1 km from Ashland Show on Map

                                        (1) Excellent 

                                          26

                                          ***2BR/2BA Beautiful Mountain Views, Close to Mtn & Downtown***

                                          Catskill Region / Windham

                                          Windham house

                                          2 5 2 nights min

                                          • 2 bedrooms
                                          • sleeps 5
                                          • 2 nights min
                                          • Child Friendly
                                          • Pet Friendly

                                          Price per night from

                                          $200

                                          Responds fast!
                                          avg. 2 hours 2 minutes

                                          Price per night from

                                          $200

                                          Distance approx 3.41 km from Ashland Show on Map

                                          (1) Excellent 

                                            34

                                            New!!! Catskills Country House (4 Bedroom) w/ Game Room

                                            New York / Prattsville

                                            Prattsville house

                                            4 10 2 nights min

                                            • 4 bedrooms
                                            • sleeps 10
                                            • 2 nights min
                                            • Child Friendly
                                            • Private garden

                                            Price per night from

                                            $434

                                            Price per night from

                                            $434

                                            Distance approx 15.79 km from Ashland

                                            (2) Excellent 

                                              14

                                              charming woodstock cottage with outdoor hottub

                                              New York / Willow

                                              Willow cottage

                                              2 4 2 nights min

                                              • 2 bedrooms
                                              • sleeps 4
                                              • 2 nights min
                                              • Child Friendly
                                              • Pet Friendly

                                              Price per night from

                                              $200

                                              Price per night from

                                              $200

                                              Distance approx 10.02 km from Ashland

                                                15

                                                Charming home with mountain views

                                                Catskill Region / Hunter

                                                Hunter house

                                                3 6 2 nights min

                                                • 3 bedrooms
                                                • sleeps 6
                                                • 2 nights min
                                                • Swimming pool
                                                • Ski
                                                • Child Friendly

                                                Price per night from

                                                $343

                                                Price per night from

                                                $343

                                                Distance approx 9.45 km from Ashland

                                                (1) Very Good 

                                                  11

                                                  Across from Hunter Mountain

                                                  Catskill Region / Hunter

                                                  Hunter apartment

                                                  3 5 min stay varies

                                                  • 3 bedrooms
                                                  • sleeps 5
                                                  • min stay varies
                                                  • Child Friendly

                                                  Price per night from

                                                  $229

                                                  Responds fast!
                                                  avg. 34 minutes

                                                  Price per night from

                                                  $229

                                                  Distance approx 14.33 km from Ashland

                                                  (1) Excellent 

                                                    28

                                                    Top of the Pass. Cozy Craftsman Style

                                                    Catskill Region / Hunter

                                                    Hunter house

                                                    4 6 2 nights min

                                                    • 4 bedrooms
                                                    • sleeps 6
                                                    • 2 nights min
                                                    • Beach / lakeside relaxation
                                                    • Nearest beach 2 mi
                                                    • Suitable for children age 5+

                                                    Price per night from

                                                    $200

                                                    Responds fast!
                                                    avg. 3 hours 20 minutes

                                                    Price per night from

                                                    $200

                                                    Distance approx 15.22 km from Ashland

                                                    (2) Excellent 

                                                      21

                                                      Catskill Region Vacation Log Home Rental

                                                      Catskill Region / Halcottsville

                                                      Halcottsville house

                                                      2 4 2 nights min

                                                      • 2 bedrooms
                                                      • sleeps 4
                                                      • 2 nights min
                                                      • Nearest beach 15 mi
                                                      • Child Friendly
                                                      • Air conditioning

                                                      Price per night from

                                                      $257

                                                      Price per night from

                                                      $257

                                                      Distance approx 4.38 km from Ashland Show on Map

                                                        24

                                                        NEW! Catskills Area Loft-Style Condo in Downtown!

                                                        Catskill Region / Windham

                                                        Windham studio

                                                        Studio 6 min stay varies

                                                        • Studio
                                                        • sleeps 6
                                                        • min stay varies
                                                        • Ski
                                                        • Child Friendly
                                                        • Air conditioning

                                                        Price per night from

                                                        $183

                                                        Responds fast!
                                                        avg. 33 minutes

                                                        Price per night from

                                                        $183

                                                        Distance approx 19.31 km from Ashland

                                                        (1) Very Good 

                                                          18

                                                          Catskill Victorian Fireplaces/ Hot Tub sleeps 12

                                                          Catskill Region / Margaretville

                                                          Margaretville house

                                                          4 12 2 nights min

                                                          • 4 bedrooms
                                                          • sleeps 12
                                                          • 2 nights min
                                                          • Child Friendly
                                                          • Air conditioning
                                                          • Private garden

                                                          Price per night from

                                                          $514

                                                          Price per night from

                                                          $514

                                                          Distance approx 18.84 km from Ashland

                                                          (6) Excellent 

                                                            30

                                                            Pet Friendly Cabin Doh-Ray Up At 1450ft

                                                            Catskill Region / Woodstock

                                                            Woodstock house

                                                            2 5 min stay varies

                                                            • 2 bedrooms
                                                            • sleeps 5
                                                            • min stay varies
                                                            • Ski
                                                            • Child Friendly
                                                            • Pet Friendly
                                                            “Relaxing mountain retreat” We enjoyed a very pleasant Thanksgiving week getaway at the cabin, which looks just like the pictures -- nice combination of modern and rustic design. Also very comfortable, clean and well organized. Tv and sound system very

                                                            Price per night from

                                                            $280

                                                            Responds fast!
                                                            avg. 41 minutes

                                                            Price per night from

                                                            $280

                                                            Distance approx 4.66 km from Ashland Show on Map

                                                              34

                                                              The Mountain House: The Perfect 4 Season Retreat

                                                              Catskill Region / Windham

                                                              Windham chalet

                                                              8 22 3 nights min

                                                              • 8 bedrooms
                                                              • sleeps 22
                                                              • 3 nights min
                                                              • Ski
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $2,856

                                                              Price per night from

                                                              $2,856

                                                              Distance approx 3.66 km from Ashland Show on Map

                                                              (3) Average 

                                                                5

                                                                Windham Cabin

                                                                New York / Lexington

                                                                Lexington log cabin

                                                                3 6 2 nights min

                                                                • 3 bedrooms
                                                                • sleeps 6
                                                                • 2 nights min
                                                                • Nearest beach 24 mi
                                                                • Child Friendly
                                                                • Air conditioning

                                                                Price per night from

                                                                $172

                                                                Price per night from

                                                                $172

                                                                Distance approx 15.57 km from Ashland

                                                                (25) Very Good 

                                                                Certificate of Excellence

                                                                  17

                                                                  Belleayre Cozy Cabin

                                                                  Catskill Region / Fleischmanns

                                                                  Fleischmanns log cabin

                                                                  1 4 2 nights min

                                                                  • 1 bedroom
                                                                  • sleeps 4
                                                                  • 2 nights min
                                                                  • Ask about children
                                                                  • Pet Friendly

                                                                  Certificate of Excellence

                                                                  Price per night from

                                                                  $143

                                                                  Responds fast!
                                                                  avg. 3 hours 7 minutes

                                                                  Price per night from

                                                                  $143

                                                                  Distance approx 6.1 km from Ashland Show on Map

                                                                  (4) Very Good 

                                                                    23

                                                                    On A Road Less Traveled -Catskill Mountain Retreat

                                                                    New York / Lexington

                                                                    Lexington house

                                                                    3 10 min stay varies

                                                                    • 3 bedrooms
                                                                    • sleeps 10
                                                                    • min stay varies
                                                                    • Child Friendly
                                                                    • Car not necessary
                                                                    • Air conditioning
                                                                    “Great place to get away” The house very clean inside and had everything we wanted. The outside had a huge deck, as well as a hot tub for extreme relaxation and tranquility. Would definitely go back.

                                                                    Price per night from

                                                                    $246

                                                                    Price per night from

                                                                    $246

                                                                    Distance approx 8.83 km from Ashland

                                                                    (8) Excellent 

                                                                      11

                                                                      Expanded Cabin facing Hunter Mountain in NY

                                                                      Catskill Region / Hunter

                                                                      Hunter log cabin

                                                                      4 7 2 nights min

                                                                      • 4 bedrooms
                                                                      • sleeps 7
                                                                      • 2 nights min
                                                                      • Beach / lakeside relaxation
                                                                      • Child Friendly
                                                                      • Car not necessary
                                                                      “Love it--would return again!” Jeffrey was very friendly, accommodating, helpful and professional as we were booking the cabin. Cabin was beautifully furnished and large enough to fit 8 of us. 5 min drive to Hunter Mountain. Very cozy and comfortabl

                                                                      Price per night from

                                                                      $686

                                                                      Responds fast!
                                                                      avg. 2 hours 38 minutes

                                                                      Price per night from

                                                                      $686

                                                                      Distance approx 10 km from Ashland

                                                                        10

                                                                        Condo with fireplace 5 min drive to Hunter Mountain ski slopes

                                                                        Catskill Region / Hunter

                                                                        Hunter condo

                                                                        1 4 1 night min

                                                                        • 1 bedroom
                                                                        • sleeps 4
                                                                        • 1 night min
                                                                        • Swimming pool
                                                                        • Child Friendly
                                                                        • Air conditioning

                                                                        Price per night from

                                                                        $115

                                                                        Price per night from

                                                                        $115

                                                                        Distance approx 17.86 km from Ashland

                                                                          13

                                                                          Charming home in the Catskills

                                                                          New York / Arkville

                                                                          Arkville house

                                                                          2 6 2 nights min

                                                                          • 2 bedrooms
                                                                          • sleeps 6
                                                                          • 2 nights min
                                                                          • Child Friendly
                                                                          • Air conditioning
                                                                          • Ask about pets

                                                                          Price per night from

                                                                          $143

                                                                          Responds fast!
                                                                          avg. 2 hours 24 minutes

                                                                          Price per night from

                                                                          $143

                                                                          Distance approx 19.8 km from Ashland

                                                                          (1) Excellent 

                                                                            54

                                                                            Woodstock Stone Cottage Swim Lake 3 ski resorts fishing hiking biking music arts

                                                                            Catskill Region / Woodstock

                                                                            Woodstock house

                                                                            4 8 2 nights min

                                                                            • 4 bedrooms
                                                                            • sleeps 8
                                                                            • 2 nights min
                                                                            • Beach / lakeside relaxation
                                                                            • Ski
                                                                            • Child Friendly

                                                                            Price per night from

                                                                            $452

                                                                            Responds fast!
                                                                            avg. 2 hours 14 minutes

                                                                            Price per night from

                                                                            $452

                                                                            Distance approx 6.94 km from Ashland Show on Map

                                                                            (1) Excellent 

                                                                              34

                                                                              Catskill Mountain Getaway - Where Memories R Made

                                                                              Catskill Region / West Kill

                                                                              West Kill house

                                                                              3 10 min stay varies

                                                                              • 3 bedrooms
                                                                              • sleeps 10
                                                                              • min stay varies
                                                                              • Child Friendly
                                                                              • Air conditioning
                                                                              • Pet Friendly

                                                                              Price per night from

                                                                              $337

                                                                              Price per night from

                                                                              $337