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21 Houses

(4) Excellent 

    21

    Beautiful Lake Side Getaway, Quiet, and Peaceful

    New Hampshire / Winchester

    Winchester apartment

    2 6 min stay varies

    • 2 bedrooms
    • sleeps 6
    • min stay varies
    • Beach / lakeside relaxation
    • Nearest beach 160 mi
    • Ask about children
    “Relaxing vacation” We vacationed here for the first two weeks of July. Bill and Sandy were fabulous hosts. They were attentive to our needs and generous with their time taking us out in their boat to view the fireworks. The space is decorated taste

    Price per night from

    $114

    Price per night from

    $114

      17

      Stay at a Craft Brewery

      New Hampshire / Winchester

      Winchester apartment

      1 2 1 night min

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

      Price per night from

      $115

      Price per night from

      $115

        15

        Stunning Forest Lake Home with Hot Tub open all Yr

        New Hampshire / Winchester

        Winchester house

        4 10 min stay varies

        • 4 bedrooms
        • sleeps 10
        • min stay varies
        • Beach / lakeside relaxation
        • Child Friendly
        • Air conditioning

        Price per night from

        $223

        Responds fast!
        avg. 2 hours 31 minutes

        Price per night from

        $223

        Great rentals within 20 miles that match your search

        Distance approx 8.45 km from Winchester Show on Map

        (1) Excellent 

          12

          Classic New England Farm House

          New Hampshire / Chesterfield

          Chesterfield b and b

          1 2 2 nights min

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

          Price per night from

          $52

          Responds fast!
          avg. 2 hours 43 minutes

          Price per night from

          $52

          Distance approx 9.39 km from Winchester Show on Map

          (1) Excellent 

            26

            Steps to the sandy beach

            New Hampshire / Spofford

            Spofford house

            3 6 min stay varies

            • 3 bedrooms
            • sleeps 6
            • min stay varies
            • Beach / lakeside relaxation
            • Ask about children
            • Air conditioning

            Price per night from

            $149

            Price per night from

            $149

            Distance approx 9.38 km from Winchester Show on Map

            (4) Excellent 

              40

              Affordable Spacious Vacation Home on Lake Spofford

              New Hampshire / Chesterfield

              Chesterfield house

              3 7 min stay varies

              • 3 bedrooms
              • sleeps 7
              • min stay varies
              • Beach / lakeside relaxation
              • Ask about children
              • Air conditioning

              Price per night from

              $119

              Price per night from

              $119

              Distance approx 13.77 km from Winchester

              (7) Excellent 

                5

                Vermont Log Cabin available for weekend and weekly

                Vermont / Guilford

                Guilford log cabin

                2 5 2 nights min

                • 2 bedrooms
                • sleeps 5
                • 2 nights min
                • Pet Friendly
                “Hidden Gem” My boyfriend and I had the pleasure of staying at this beautiful cabin a couple of weeks ago and honestly, I can't say enough good things about it! For starters, it is gorgeous both inside and out and much bigger than we had anticipated.

                Price per night from

                $126

                Price per night from

                $126

                Distance approx 9.4 km from Winchester Show on Map

                (32) Very Good 

                  40

                  Beautiful House overlooking Spofford Lake

                  New Hampshire / Spofford

                  Spofford house

                  4 10 min stay varies

                  • 4 bedrooms
                  • sleeps 10
                  • min stay varies
                  • Beach / lakeside relaxation
                  • Ask about children
                  • Air conditioning

                  Price per night from

                  $183

                  Price per night from

                  $183

                  Distance approx 10.51 km from Winchester

                    15

                    Enchanting Rockwood Pond Home with Hot Tub!

                    New Hampshire / Fitzwilliam

                    Fitzwilliam house

                    3 10 min stay varies

                    • 3 bedrooms
                    • sleeps 10
                    • min stay varies
                    • Beach / lakeside relaxation
                    • Child Friendly
                    • Air conditioning

                    Price per night from

                    $223

                    Responds fast!
                    avg. 2 hours 31 minutes

                    Price per night from

                    $223

                    Distance approx 18.4 km from Winchester

                    (1) Excellent 

                      7

                      PARADISE on EARTH! - Historic 4BR Farmhouse

                      Vermont / West Halifax

                      West Halifax house

                      4 8 3 nights min

                      • 4 bedrooms
                      • sleeps 8
                      • 3 nights min
                      • Child Friendly
                      • Ask about pets
                      • Private garden

                      Price per night from

                      $325

                      Price per night from

                      $325

                      Distance approx 9.71 km from Winchester

                        7

                        Historic Lakefront Spofford Cottage

                        New Hampshire / Spofford

                        Spofford house

                        4 8 7 nights min

                        • 4 bedrooms
                        • sleeps 8
                        • 7 nights min
                        • Child Friendly
                        • Private garden

                        Price per night from

                        $457

                        Responds fast!
                        avg. 40 minutes

                        Price per night from

                        $457

                        Distance approx 15.91 km from Winchester

                          16

                          Church sanctuary

                          Vermont / West Dummerston

                          West Dummerston house

                          3 6 2 nights min

                          • 3 bedrooms
                          • sleeps 6
                          • 2 nights min
                          • Ask about children

                          Price per night from

                          $297

                          Price per night from

                          $297

                          Distance approx 18.35 km from Winchester

                            26

                            Serene Shelburne Studio Cabin w/Spring-Fed Pool!

                            Massachusetts / Shelburne Falls

                            Shelburne Falls studio

                            Studio 6 min stay varies

                            • Studio
                            • sleeps 6
                            • min stay varies
                            • Swimming pool
                            • Ski
                            • Child Friendly

                            Price per night from

                            $189

                            Responds fast!
                            avg. 41 minutes

                            Price per night from

                            $189

                            Distance approx 18.53 km from Winchester

                            (1) Excellent 

                              15

                              3 BDR Farmhouse on Tranquil 105 acre Organic Farm

                              New Hampshire / Walpole

                              Walpole house

                              3 8 3 nights min

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

                              Price per night from

                              $302

                              Price per night from

                              $302

                              Distance approx 8.45 km from Winchester Show on Map

                                12

                                Historical Farm House

                                New Hampshire / Chesterfield

                                Chesterfield b and b

                                1 2 2 nights min

                                • 1 bedroom
                                • sleeps 2
                                • 2 nights min
                                • Child Friendly
                                • Air conditioning
                                • Private garden

                                Price per night from

                                $52

                                Responds fast!
                                avg. 1 hour 10 minutes

                                Price per night from

                                $52

                                Distance approx 16.85 km from Winchester

                                  18

                                  Penthouse at Brandt House B&B

                                  Massachusetts / Greenfield

                                  Greenfield b and b

                                  1 4 2 nights min

                                  • 1 bedroom
                                  • sleeps 4
                                  • 2 nights min
                                  • Child Friendly

                                  Price per night from

                                  $285

                                  Price per night from

                                  $285

                                  Distance approx 16.05 km from Winchester

                                  (5) Excellent 

                                    32

                                    Stone 'n Sky Lodge on an Ancient Stone Landscape

                                    Massachusetts / New Salem

                                    New Salem house

                                    4 14 2 nights min

                                    • 4 bedrooms
                                    • sleeps 14
                                    • 2 nights min
                                    • Nearest beach 5 mi
                                    • Child Friendly
                                    • Ask about pets

                                    Price per night from

                                    $326

                                    Price per night from

                                    $326

                                    Distance approx 11.75 km from Winchester

                                    (2) Average 

                                      5

                                      Adorable Studio apartment in Brattleboro

                                      Vermont / Brattleboro

                                      Brattleboro apartment

                                      2 1 night min

                                      • sleeps 2
                                      • 1 night min
                                      • Ask about children
                                      • Pet Friendly

                                      Price per night from

                                      $155

                                      Price per night from

                                      $155

                                      Distance approx 19.87 km from Winchester

                                        24

                                        Cobb Hill Estate - 6 brs sleeps 15 on 750 acres!

                                        New Hampshire / Harrisville

                                        Harrisville villa

                                        6 15 min stay varies

                                        • 6 bedrooms
                                        • sleeps 15
                                        • min stay varies
                                        • Ask about children

                                        Price per night from

                                        $548

                                        Responds fast!
                                        avg. 1 hour 28 minutes

                                        Price per night from

                                        $548

                                        Distance approx 11.5 km from Winchester

                                          30

                                          Colonial Keene House on 7 Acres w/ Pool!

                                          New Hampshire / Keene

                                          Keene house

                                          9 18 min stay varies

                                          • 9 bedrooms
                                          • sleeps 18
                                          • min stay varies
                                          • Swimming pool
                                          • Ski
                                          • Child Friendly

                                          Price per night from

                                          $453

                                          Responds fast!
                                          avg. 39 minutes

                                          Price per night from

                                          $453

                                          Distance approx 12.65 km from Winchester

                                            28

                                            NEW! Beautiful Log House 3.5 Mi. to Spofford Lake!

                                            New Hampshire / Westmoreland

                                            Westmoreland house

                                            2 4 min stay varies

                                            • 2 bedrooms
                                            • sleeps 4
                                            • min stay varies
                                            • Air conditioning

                                            Price per night from

                                            $161

                                            Responds fast!
                                            avg. 39 minutes

                                            Price per night from

                                            $161