Vacation Rentals & Apartments in Woodstock

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242 apartments

(3) Excellent 

    29

    Margaret's Cottage in Woodstock Village

    Catskill Region / Woodstock

    Woodstock log cabin

    2 4 2 nights min

    • 2 bedrooms
    • sleeps 4
    • 2 nights min
    • Child Friendly
    • Car not necessary
    • Air conditioning

    Price per night from

    $189

    Price per night from

    $189

    (1) Excellent 

      19

      Fabulous Family House nr Woodstock Center

      Catskill Region / Woodstock

      Woodstock house

      4 8 min stay varies

      • 4 bedrooms
      • sleeps 8
      • min stay varies
      • Ski
      • Child Friendly

      Price per night from

      $279

      Price per night from

      $279

      (1) Excellent 

        13

        Teahouse Cottage

        Catskill Region / Woodstock

        Woodstock cottage

        50 4 1 night min

        • 50 bedrooms
        • sleeps 4
        • 1 night min
        • Child Friendly
        • Air conditioning
        • Pet Friendly

        Price per night from

        $178

        Responds fast!
        avg. 3 hours 6 minutes

        Price per night from

        $178

        (3) Excellent 

          82

          New Hot Tub & Heated Pool in Prime Woodstock Gut Renovated Modern Home

          Catskill Region / Woodstock

          Woodstock house

          5 13 min stay varies

          • 5 bedrooms
          • sleeps 13
          • min stay varies
          • Swimming pool
          • Child Friendly
          • Air conditioning

          Price per night from

          $373

          Responds fast!
          avg. 50 minutes

          Price per night from

          $373

          (47) Excellent 

            23

            Woodstock In-town cottage

            Catskill Region / Woodstock

            Woodstock cottage

            1 2 2 nights min

            • 1 bedroom
            • sleeps 2
            • 2 nights min
            • Beach / lakeside relaxation
            • Nearest beach 6 mi
            • Car not necessary
            “Perfect” This little gem was the perfect getaway for me, my friend and my dog Amber. The location was private yet walking distance into town, near a beautiful stream and gentle, peaceful hiking trails. The owners El and Eric personally met us when we
            …see more

            Price per night from

            $172

            Responds fast!
            avg. 7 minutes

            Price per night from

            $172

            (5) Excellent 

              36

              Mid Century Ranch-Hot Tub-Minutes to Center ofTown

              Catskill Region / Woodstock

              Woodstock house

              4 8 3 nights min

              • 4 bedrooms
              • sleeps 8
              • 3 nights min
              • Nearest beach 1 mi
              • Child Friendly
              • Air conditioning

              Price per night from

              $401

              Responds fast!
              avg. 2 hours 43 minutes

              Price per night from

              $401

                24

                Event-Friendly Home - 5 Mins to Central Woodstock

                Catskill Region / Woodstock

                Woodstock house

                2 6 min stay varies

                • 2 bedrooms
                • sleeps 6
                • min stay varies
                • Child Friendly
                • Air conditioning

                Price per night from

                $166

                Responds fast!
                avg. 3 hours 34 minutes

                Price per night from

                $166

                  14

                  Tranquil Woodstock Home in the Woods with Hot Tub and Ping Pong

                  Catskill Region / Woodstock

                  Woodstock house

                  2 4 2 nights min

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

                  Price per night from

                  $338

                  Price per night from

                  $338

                  (5) Very Good 

                    10

                    Woodstock Village Serene & Spacious

                    Catskill Region / Woodstock

                    Woodstock house

                    2 6 1 night min

                    • 2 bedrooms
                    • sleeps 6
                    • 1 night min
                    • Ask about children
                    • Air conditioning
                    • Ask about pets

                    Price per night from

                    $258

                    Responds fast!
                    avg. 3 hours 55 minutes

                    Price per night from

                    $258

                    (3) Excellent 

                      22

                      Woodstock Cottage: walk to Town

                      Catskill Region / Woodstock

                      Woodstock cottage

                      2 4 2 nights min

                      • 2 bedrooms
                      • sleeps 4
                      • 2 nights min
                      • Beach / lakeside relaxation
                      • Child Friendly
                      • Car not necessary
                      “Very well kept and extremely caring owners” The cottage seems as though it was renovated yesterday because it is so clean and well kept. The kitchen has everything you need to cook, and the living room is comfortable. There are many games and movies a
                      …see more

                      Price per night from

                      $361

                      Responds fast!
                      avg. 3 hours 18 minutes

                      Price per night from

                      $361

                        14

                        Charming Converted Barn On 2+ Acres Walk To Town

                        Catskill Region / Woodstock

                        Woodstock house

                        5 10 2 nights min

                        • 5 bedrooms
                        • sleeps 10
                        • 2 nights min
                        • Child Friendly
                        • Air conditioning

                        Price per night from

                        $487

                        Price per night from

                        $487

                        (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
                          …see more

                          Price per night from

                          $292

                          Responds fast!
                          avg. 1 hour 8 minutes

                          Price per night from

                          $292

                            17

                            Woodstock Peace, Privacy, Views

                            Catskill Region / Woodstock

                            Woodstock house

                            4 9 3 nights min

                            • 4 bedrooms
                            • sleeps 9
                            • 3 nights min
                            • Swimming pool
                            • Ask about children
                            • Air conditioning

                            Price per night from

                            $1,145

                            Price per night from

                            $1,145

                              24

                              Woodstock Oasis. 3 acres of secluded nature. Walkable to town

                              Catskill Region / Woodstock

                              Woodstock house

                              4 8 3 nights min

                              • 4 bedrooms
                              • sleeps 8
                              • 3 nights min
                              • Child Friendly

                              Price per night from

                              $252

                              Price per night from

                              $252

                              (3) Excellent 

                                26

                                Woodstock Mediterranean Retreat

                                Catskill Region / Woodstock

                                Woodstock house

                                4 11 min stay varies

                                • 4 bedrooms
                                • sleeps 11
                                • min stay varies
                                • Swimming pool
                                • Child Friendly
                                • Air conditioning

                                Price per night from

                                $516

                                Price per night from

                                $516

                                (4) Excellent 

                                  30

                                  Stunning Vacation Country & Ski House

                                  Catskill Region / Woodstock

                                  Woodstock house

                                  4 12 min stay varies

                                  • 4 bedrooms
                                  • sleeps 12
                                  • min stay varies
                                  • Child Friendly
                                  • Ask about pets
                                  • Private garden
                                  “One of a kind, secluded, comfortable, & friendly.” We had the best weekend here in this beautiful spacious house. The huge windows all around the living area give such a peaceful feeling looking at the forst or the stream in the backyard. We enjoyed f
                                  …see more

                                  Price per night from

                                  $516

                                  Responds fast!
                                  avg. 1 hour 31 minutes

                                  Price per night from

                                  $516

                                  (1) Excellent 

                                    31

                                    Wonderful Woodstock Garden House w large firepit!

                                    Catskill Region / Woodstock

                                    Woodstock house

                                    3 6 min stay varies

                                    • 3 bedrooms
                                    • sleeps 6
                                    • min stay varies
                                    • Child Friendly
                                    • Air conditioning
                                    • Private garden

                                    Price per night from

                                    $258

                                    Price per night from

                                    $258

                                    (8) Excellent 

                                      31

                                      Woodstock-Pool, Hot Tub, Stream; 7 Acres; Hike&Ski

                                      Catskill Region / Woodstock

                                      Woodstock house

                                      3 8 min stay varies

                                      • 3 bedrooms
                                      • sleeps 8
                                      • min stay varies
                                      • Swimming pool
                                      • Child Friendly
                                      • Air conditioning

                                      Price per night from

                                      $338

                                      Responds fast!
                                      avg. 1 hour 55 minutes

                                      Price per night from

                                      $338

                                        30

                                        'Casa Reál' Expansive Woodstock House w/ Hot Tub!

                                        Catskill Region / Woodstock

                                        Woodstock house

                                        4 8 min stay varies

                                        • 4 bedrooms
                                        • sleeps 8
                                        • min stay varies
                                        • Ski
                                        • Child Friendly
                                        • Air conditioning

                                        Price per night from

                                        $332

                                        Responds fast!
                                        avg. 47 minutes

                                        Price per night from

                                        $332

                                          25

                                          Sun Salutations in Woodstock, a mile to the village & a stop on Trailways

                                          Catskill Region / Woodstock

                                          Woodstock house

                                          4 8 2 nights min

                                          • 4 bedrooms
                                          • sleeps 8
                                          • 2 nights min
                                          • Child Friendly
                                          • Air conditioning
                                          • Pet Friendly

                                          Price per night from

                                          $286

                                          Responds fast!
                                          avg. 2 hours 8 minutes

                                          Price per night from

                                          $286

                                          (1) Excellent 

                                            37

                                            Woodstock Modern House with a Pool

                                            Catskill Region / Woodstock

                                            Woodstock house

                                            4 10 2 nights min

                                            • 4 bedrooms
                                            • sleeps 10
                                            • 2 nights min
                                            • Swimming pool
                                            • Ski
                                            • Child Friendly

                                            Price per night from

                                            $401

                                            Price per night from

                                            $401

                                            (3) Excellent 

                                              13

                                              Cozy & Serene Cottage in Woodstock

                                              Catskill Region / Woodstock

                                              Woodstock cottage

                                              1 3 2 nights min

                                              • 1 bedroom
                                              • sleeps 3
                                              • 2 nights min
                                              • Child Friendly
                                              • Air conditioning
                                              • Pet Friendly

                                              Price per night from

                                              $229

                                              Price per night from

                                              $229

                                                19

                                                Woodstock gorgeous cottage & pool. on 10 acres

                                                Catskill Region / Woodstock

                                                Woodstock house

                                                2 6 2 nights min

                                                • 2 bedrooms
                                                • sleeps 6
                                                • 2 nights min
                                                • Beach / lakeside relaxation
                                                • Swimming pool
                                                • Child Friendly

                                                Price per night from

                                                $373

                                                Price per night from

                                                $373

                                                  14

                                                  Woodstock Carriage House

                                                  Catskill Region / Woodstock

                                                  Woodstock house

                                                  4 6 2 nights min

                                                  • 4 bedrooms
                                                  • sleeps 6
                                                  • 2 nights min
                                                  • Child Friendly
                                                  • Private garden

                                                  Price per night from

                                                  $229

                                                  Responds fast!
                                                  avg. 13 minutes

                                                  Price per night from

                                                  $229

                                                  (1) Excellent 

                                                    22

                                                    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

                                                    $453

                                                    Responds fast!
                                                    avg. 2 hours 3 minutes

                                                    Price per night from

                                                    $453

                                                      17

                                                      Spacious Family Retreat, Woodstock, 2hrs from NYC

                                                      Catskill Region / Woodstock

                                                      Woodstock house

                                                      4 9 2 nights min

                                                      • 4 bedrooms
                                                      • sleeps 9
                                                      • 2 nights min
                                                      • Child Friendly
                                                      • Air conditioning
                                                      • Private garden

                                                      Price per night from

                                                      $292

                                                      Price per night from

                                                      $292

                                                      (9) Very Good 

                                                        26

                                                        Olive Oasis Luxury with Hot Tub, Woodstock Area

                                                        Catskill Region / Woodstock

                                                        Woodstock house

                                                        3 6 2 nights min

                                                        • 3 bedrooms
                                                        • sleeps 6
                                                        • 2 nights min
                                                        • Child Friendly
                                                        • Air conditioning
                                                        • Pet Friendly
                                                        “Lovely weekend retreat” Spent two relaxing, lovely nights at the Olive Oasis. The house was clean and big, in a quiet and green neighbourhood. Loved the hottub, fire-pit and yoga studio, made for a great weekend away! Dina was easy to communicate with
                                                        …see more

                                                        Price per night from

                                                        $220

                                                        Responds fast!
                                                        avg. 1 hour 27 minutes

                                                        Price per night from

                                                        $220

                                                          8

                                                          Woodstock Town Center Studio Apt.

                                                          Catskill Region / Woodstock

                                                          Woodstock apartment

                                                          1 2 2 nights min

                                                          • 1 bedroom
                                                          • sleeps 2
                                                          • 2 nights min
                                                          • Air conditioning

                                                          Price per night from

                                                          $132

                                                          Price per night from

                                                          $132

                                                            15

                                                            Mountain Woodland Private Elegant Peacefull MAGIC

                                                            Catskill Region / Woodstock

                                                            Woodstock house

                                                            3 6 3 nights min

                                                            • 3 bedrooms
                                                            • sleeps 6
                                                            • 3 nights min
                                                            • Swimming pool
                                                            • Child Friendly
                                                            • Air conditioning

                                                            Price per night from

                                                            $544

                                                            Price per night from

                                                            $544

                                                              33

                                                              Relax by the pool at Serenity Villa then take a dip in the hot tub!

                                                              Catskill Region / Woodstock

                                                              Woodstock house

                                                              3 8 min stay varies

                                                              • 3 bedrooms
                                                              • sleeps 8
                                                              • min stay varies
                                                              • Swimming pool
                                                              • Child Friendly
                                                              • Air conditioning

                                                              Price per night from

                                                              $430

                                                              Price per night from

                                                              $430

                                                              (2) Very Good 

                                                                22

                                                                Woodstock Retreat, Sauna, Steam Shower, Decks

                                                                Catskill Region / Woodstock

                                                                Woodstock house

                                                                2 8 3 nights min

                                                                • 2 bedrooms
                                                                • sleeps 8
                                                                • 3 nights min
                                                                • Child Friendly
                                                                • Air conditioning
                                                                • Pet Friendly

                                                                Price per night from

                                                                $338

                                                                Responds fast!
                                                                avg. 2 hours 3 minutes

                                                                Price per night from

                                                                $338

                                                                  14

                                                                  Schoolhouse Cottage

                                                                  Catskill Region / Woodstock

                                                                  Woodstock house

                                                                  1 4 1 night min

                                                                  • 1 bedroom
                                                                  • sleeps 4
                                                                  • 1 night min
                                                                  • Child Friendly
                                                                  • Pet Friendly

                                                                  Price per night from

                                                                  $218

                                                                  Responds fast!
                                                                  avg. 3 hours 6 minutes

                                                                  Price per night from

                                                                  $218

                                                                    20

                                                                    Historic Southwestern Chalet

                                                                    Catskill Region / Woodstock

                                                                    Woodstock house

                                                                    4 12 min stay varies

                                                                    • 4 bedrooms
                                                                    • sleeps 12
                                                                    • min stay varies
                                                                    • Child Friendly

                                                                    Price per night from

                                                                    $401

                                                                    Price per night from

                                                                    $401

                                                                      26

                                                                      Spectacular Mountaintop Estate

                                                                      Catskill Region / Woodstock

                                                                      Woodstock apartment

                                                                      4 10 min stay varies

                                                                      • 4 bedrooms
                                                                      • sleeps 10
                                                                      • min stay varies
                                                                      • Child Friendly

                                                                      Price per night from

                                                                      $540

                                                                      Price per night from

                                                                      $540

                                                                      (1)  

                                                                        12

                                                                        Sioux Tipi on the waterfall

                                                                        Catskill Region / Woodstock

                                                                        Woodstock tipi/teepee

                                                                        1 4 1 night min

                                                                        • 1 bedroom
                                                                        • sleeps 4
                                                                        • 1 night min
                                                                        • Child Friendly
                                                                        • Pet Friendly
                                                                        • Private garden

                                                                        Price per night from

                                                                        $172

                                                                        Responds fast!
                                                                        avg. 3 hours 6 minutes

                                                                        Price per night from

                                                                        $172

                                                                          28

                                                                          Relaxing Zen Cabin

                                                                          Catskill Region / Woodstock

                                                                          Woodstock house

                                                                          1 4 min stay varies

                                                                          • 1 bedroom
                                                                          • sleeps 4
                                                                          • min stay varies
                                                                          • Child Friendly

                                                                          Price per night from

                                                                          $180

                                                                          Price per night from

                                                                          $180

                                                                            49

                                                                            Peaceful Woodstock Retreat - Restored Barn

                                                                            Catskill Region / Woodstock

                                                                            Woodstock barn

                                                                            3 6 2 nights min

                                                                            • 3 bedrooms
                                                                            • sleeps 6
                                                                            • 2 nights min
                                                                            • Child Friendly
                                                                            • Air conditioning
                                                                            • Pet Friendly

                                                                            Price per night from

                                                                            $457

                                                                            Price per night from

                                                                            $457

                                                                              4

                                                                              Glamping at Woodstock Meadows - Outdoor B&B (2 secluded tents w/amenities)

                                                                              Catskill Region / Woodstock

                                                                              Woodstock tented camp

                                                                              2 4 2 nights min

                                                                              • 2 bedrooms
                                                                              • sleeps 4
                                                                              • 2 nights min

                                                                              Price per night from

                                                                              $227

                                                                              Price per night from

                                                                              $227

                                                                              About Woodstock

                                                                              With a surprisingly large arts community, rolling green hills, and friendly locals, the small and picturesque town of Woodstock has it all! The primary street that hosts a row of boutiques and charming restaurants is known as Tinker Street, but don't limit yourself to this one area. There are plenty of things to see and do across the entire town.

                                                                              Here are just a few additional suggestions of things to do in Woodstock:

                                                                              • Shawangunk Mountains: This mountain range attracts people from all over the area with its rock climbing, hiking, and camping options.
                                                                              • SweetHeart Gallery: Overlooking a beautiful waterfall, this popular local gallery features artwork and crafts pieces from some of the best artists in the region.
                                                                              • Karma Triyana Dharmachakra Tibetan Buddhist Monastery: This beautiful and serene monastery is the perfect place to spend an afternoon learning about Buddhism or just simply clearing your head.

                                                                              For those looking to attend local events and festivals, head to Ulster County, a short drive from Woodstock. In Ulster County you can cheer on the competitors participating in the Shandaken Primitive Biathlon in January, watch the boat rally on the Wallkill River at the New Paltz Regatta in May, or take home a piece of art from one of the best artists in the region at the Woodstock-New Paltz Art and Crafts Fair in September.

                                                                              Luckily, there's a vacation rental available in Woodstock that has everything you are looking for in a getaway home. Book a luxury condo downtown or rent a secluded cabin in the woods just steps from the mountains for an unforgettable vacation experience.

                                                                              If you're looking to explore the surrounding area, there are several other towns just outside of Woodstock that make for great day trips. The busy college town of Binghamton and the rolling fields of Oswego can both be reached within an hour by car.