10 Best Vacation Rentals in Hampshire County - Holiday Lettings - Cabins

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28 Vacation rentals

    21

    Vacation farmhouse in Belchertown

    Hampshire County / Belchertown

    6 14 2 nights min

    • 6 bedrooms
    • sleeps 14
    • 2 nights min
    • Air conditioning
    This beautiful turn-of-the-century Victorian is the former rectory to a beautiful old church that is now an artist studio (The Artist Common - available for rent separately). It is secluded a top a hill on 4 1/2 acres and has soaring ceilings, period details, modern kit

    from $458 / night

    $2,290 / week

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    from $458 / night

      5

      Vacation b&b in Northampton

      Hampshire County / Northampton

      1 2 2 nights min

      • 1 bedroom
      • sleeps 2
      • 2 nights min
      • Child friendly
      The White Room has a single queen sized bed and a beautiful cherry desk built by your host, John. This room has its own bathroom (ensuite) with a shower, toilet, sink, and toiletries. Sitting at the desk, you will see the east pasture where the llamas like to sleep in t

      from $132 / night

      $922 / week

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      from $132 / night

        14

        Vacation b&b rental

        Hampshire County / Hatfield

        1 4 3 nights min

        • 1 bedroom
        • sleeps 4
        • 3 nights min
        • Ask about children
        • Air conditioning
        Very unique apartments in beautifully restored 19th-century grist mill with private dam and waterfall, available for daily, weekly or monthly stays. As little as $76/night for longer stays, and additional days are prorated based on weekly/monthly rate. All utilities, Wi

        from $229 / night

        $1,031 / week

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        from $229 / night

          7

          Vacation b&b in Northampton

          Hampshire County / Northampton

          1 2 2 nights min

          • 1 bedroom
          • sleeps 2
          • 2 nights min
          Actually, the Pink room is painted a lovely 'Santa Fe red' and is a mirror image to the White Room. The Pink room has a single queen sized bed, and its own bath in the room (ensuite) with a shower, toilet, freestanding sink, and toiletries. Sitting at the spinette (an a

          from $132 / night

          $922 / week

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          from $132 / night

          (4) Excellent 

            16

            Vacation cottage in Goshen

            Hampshire County / Goshen

            3 6 7 nights min

            • 3 bedrooms
            • sleeps 6
            • 7 nights min
            • Beach/lakeside relaxation
            • Child friendly
            • Pet friendly
            We have shared the beauty of our lakefront property for many summers. We live on the property year round and rent three cottages from late June through September.We love our guests and honor their privacy. We are a family and pet (dog) friendly vacation spot,unique an

            from $195 / night

            $1,363 / week

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            from $195 / night

              25

              Huntington Vacation home rental

              Hampshire County / Huntington

              3 7 min stay varies

              • 3 bedrooms
              • sleeps 7
              • min stay varies
              • Child friendly
              • Air conditioning
              You and your travel companions will be stricken by colonial beauty as you cross the threshold into this Huntington vacation rental home. The 3-bedroom, 2-bathroom house was constructed in 1789 and still boasts many of the original furnishings, but now features all of th

              from $218 / night

              $1,523 / week

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              Responds fast!
              avg. 3 hours 46 minutes

              from $218 / night

              (1) Excellent 

                21

                Belchertown Vacation home rental

                Hampshire County / Belchertown

                2 8 2 nights min

                • 2 bedrooms
                • sleeps 8
                • 2 nights min
                • Nearest beach 0.2 mi
                • Child friendly
                • Air conditioning
                Relax in our charming cottage while resting your eyes on peaceful Lake Arcadia. Slip into your suits & jump in across the street and use our kayaks or walk 8 minutes to bask on the town beach (open July and August only) with a concession stand, life guard & paddle boats

                from $224 / night

                $1,483 - $1,884 / week

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                from $224 / night

                (16) Very Good 

                  27

                  Ski home to rent in Plainfield

                  Hampshire County / Plainfield

                  3 10 min stay varies

                  • 3 bedrooms
                  • sleeps 10
                  • min stay varies
                  • Beach/lakeside relaxation
                  • Nearest beach 0.5 mi
                  • Ski
                  Experience a Berkshire get-away in this huge secluded luxury modern house. It's the only house that is surrounded by 10,000 Acres of protected Hawley State forest. Escape from headaches and the rat race. No cell phone reception here! But we have WiFi and a house phone.

                  from $234 / night

                  $1,575 - $2,393 / week

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                  Responds fast!
                  avg. 2 hours 51 minutes

                  from $234 / night

                    8

                    Vacation b&b in Northampton

                    Hampshire County / Northampton

                    1 2 2 nights min

                    • 1 bedroom
                    • sleeps 2
                    • 2 nights min
                    • Child friendly
                    The Lavender Room, or Inside room as we often call it, is nestled inside the house, and is located off the kitchen. It is the largest of the three rooms and was recently painted a lovely 'amethyst' or rich lavender color. Its bathroom, while not in the room, is located

                    from $132 / night

                    $922 / week

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                    from $132 / night

                      24

                      Vacation log cabin in Goshen

                      Hampshire County / Goshen

                      2 6 min stay varies

                      • 2 bedrooms
                      • sleeps 6
                      • min stay varies
                      • Child friendly
                      • Air conditioning
                      • Pet friendly
                      Escape to the New England woodlands and reconnect with the outdoors when you stay at this 2-bedroom, 1-bathroom Goshen vacation rental cabin that sleeps up to 8. This quiet, 725-square-foot cabin offers peace and comfort, with an open-concept living space, a large deck

                      from $241 / night

                      $1,684 / week

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                      Responds fast!
                      avg. 33 minutes

                      from $241 / night

                        11

                        Plainfield Vacation tented camp rental

                        Hampshire County / Plainfield

                        1 4 2 nights min

                        • 1 bedroom
                        • sleeps 4
                        • 2 nights min
                        • Child friendly
                        • Pet friendly
                        The Tentrr Berkshire Magic Woods has woodland trails from the campsite lead you to historic mill sites along a beautiful river including a swimming hole and waterfalls all within a few minutes away. This an exclusive Tentrr site. Tentrr offers fully-equipped individua

                        from $138 / night

                        $962 / week

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                        from $138 / night

                          10

                          Vacation tented camp rental

                          Hampshire County / Westhampton

                          1 4 2 nights min

                          • 1 bedroom
                          • sleeps 4
                          • 2 nights min
                          • Child friendly
                          • Pet friendly
                          The Tentrr Bron Yr Aur Campsite is a quiet mountain hideaway with picturesque views. This is an exclusive Tentrr site. Tentrr offers fully-equipped individual campsites on beautiful private land. Picturesque camp on a mountaintop. Great views! This campsite is off-the

                          from $158 / night

                          $1,106 / week

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                          from $158 / night

                            23

                            Vacation apartment in Northampton

                            Hampshire County / Northampton

                            1 4 2 nights min

                            • 1 bedroom
                            • sleeps 4
                            • 2 nights min
                            • Child friendly
                            • Car not necessary
                            • Air conditioning
                            Tibet House is a beautifully decorated and comfortably furnished private apartment on a quiet tree lined street just 3 blocks from Smith College and downtown Northampton. The Parlor Room, The Iron Horse, The Academy of Music and The Calvin Theater are all just a short w

                            from $149 / night

                            $1,042 / week

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                            from $149 / night

                              11

                              Vacation tented camp in Plainfield

                              Hampshire County / Plainfield

                              1 4 2 nights min

                              • 1 bedroom
                              • sleeps 4
                              • 2 nights min
                              • Child friendly
                              • Pet friendly
                              The Tentrr Hilltop Nook Berkshires is an amazing spot on Page Tree Farm with two streams, private trails and swimming holes. The property is a gem! You'll love the sparkly rock outcroppings. If you look carefully you can find "glacial potholes" created in ledges around

                              from $158 / night

                              $1,106 / week

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                              from $158 / night

                              Great rentals within 20 miles that match your search

                              Distance approx 14 miles from Hampshire County Show on Map

                                11

                                Vacation tented camp rental

                                Massachusetts / Conway

                                1 4 2 nights min

                                • 1 bedroom
                                • sleeps 4
                                • 2 nights min
                                • Child friendly
                                • Pet friendly
                                The Tentrr Trailside Camp at Greenhill campsite is a peaceful wooded base camp in an activity-filled area. This is an exclusive Tentrr site. Tentrr offers fully-equipped individual campsites on beautiful private land. This campsite is off-the-grid, offering the chance

                                from $158 / night

                                $1,106 / week

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                                from $158 / night

                                Distance approx 18.31 miles from Hampshire County Show on Map

                                  18

                                  B&b rental in Greenfield

                                  Massachusetts / Greenfield

                                  1 4 2 nights min

                                  • 1 bedroom
                                  • sleeps 4
                                  • 2 nights min
                                  • Child friendly
                                  Brandt House is a three-and-a-half-acre, turn-of-the-century estate located in a charming residential area of Greenfield, just minutes from I-91 and Route 2 in northwestern Massachusetts. Walking distance to downtown Greenfield and in the northern Pioneer Valley where c

                                  from $286 / night

                                  $1,603 / week

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                                  from $286 / night

                                  Distance approx 17.52 miles from Hampshire County Show on Map

                                  (1) Excellent 

                                    8

                                    Home rental in East Longmeadow

                                    Massachusetts / East Longmeadow

                                    1 2 2 nights min

                                    • 1 bedroom
                                    • sleeps 2
                                    • 2 nights min
                                    • Private garden
                                    Corner Cottage. This is a private house. It is a house-share. There are 2 adults and 2 cats living in the home. My home is very bright and sunny. My place is close to family-friendly activities, nightlife, and public transport. You’ll love my place because it is quiet

                                    from $58 / night

                                    $436 - $556 / week

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                                    from $58 / night

                                    Distance approx 18.56 miles from Hampshire County Show on Map

                                      12

                                      Vacation tented camp in Granville

                                      Berkshires / Granville

                                      1 4 2 nights min

                                      • 1 bedroom
                                      • sleeps 4
                                      • 2 nights min
                                      • Child friendly
                                      • Pet friendly
                                      The Tentrr Black Rabbit Farm has the Berkshire mountain range rising before you, this campsite is located on a very unique farm. Black Rabbit Farm offers a wide range of artisan provisions in the farm store as well as their celebrated wild ales, you will be delighting i

                                      from $154 / night

                                      $1,074 / week

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                                      from $154 / night

                                      Distance approx 15.92 miles from Hampshire County Show on Map

                                      (1) Excellent 

                                        6

                                        Vacation hotel apartment in West Springfield

                                        Massachusetts / West Springfield

                                        2 9 1 night min

                                        • 2 bedrooms
                                        • sleeps 9
                                        • 1 night min
                                        • Child friendly
                                        • Air conditioning
                                        Lily's Lodge is your Home away from Home in Western Massachusetts. We are located directly across the street from the Eastern States Exposition Fairgrounds, minutes from downtown Springfield and within 5-15 minute drive to area colleges, Basketball Hall of Fame, and Si

                                        from $194 / night

                                        $1,355 / week

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                                        from $194 / night

                                        Distance approx 18.38 miles from Hampshire County Show on Map

                                          23

                                          Vacation studio in Agawam

                                          Massachusetts / Agawam

                                          Studio 5 min stay varies

                                          • Studio
                                          • sleeps 5
                                          • min stay varies
                                          • Child friendly
                                          • Air conditioning
                                          • Pet friendly
                                          Visit Agawam in comfort when you stay at this cozy vacation rental studio that sleeps 5, only a few minutes drive south from Springfield! Complete with a well-equipped kitchen, a plush queen-sized bed and a cozy lounge area with a flat-screen cable TV, this studio is pe

                                          from $144 / night

                                          $1,002 / week

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                                          Responds fast!
                                          avg. 33 minutes

                                          from $144 / night

                                          Distance approx 17.01 miles from Hampshire County Show on Map

                                            10

                                            Vacation tented camp rental

                                            Massachusetts / Montague

                                            1 4 2 nights min

                                            • 1 bedroom
                                            • sleeps 4
                                            • 2 nights min
                                            • Child friendly
                                            • Pet friendly
                                            The Tentrr Lovely Montague Retreat campsite is an idyllic landscape located just minutes from the beautiful Montague Bookmill. This campsite is off-the-grid, offering the chance to relax, unplug, and experience nature! There is no electricity or WiFi, and cell service i

                                            from $146 / night

                                            $1,018 / week

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                                            from $146 / night

                                            Distance approx 17.24 miles from Hampshire County Show on Map

                                              11

                                              Ashfield Vacation tented camp rental

                                              Massachusetts / Ashfield

                                              1 4 2 nights min

                                              • 1 bedroom
                                              • sleeps 4
                                              • 2 nights min
                                              • Child friendly
                                              • Pet friendly
                                              The Tentrr Camp Cozie Nook is a short drive down our dirt road will lead you through a lovely valley filled with a hayfield, beautiful heritage sheep and a llama grazing leisurely and free ranging chickens and ducks. This is an exclusive Tentrr site. Tentrr offers full

                                              from $149 / night

                                              $1,042 / week

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                                              from $149 / night

                                              Distance approx 14.98 miles from Hampshire County Show on Map

                                                24

                                                Vacation home in Springfield

                                                Massachusetts / Springfield

                                                2 6 2 nights min

                                                • 2 bedrooms
                                                • sleeps 6
                                                • 2 nights min
                                                • Child friendly
                                                • Air conditioning
                                                Book your Springfield getaway to 'Lil Lubb's Layout,' a recently updated 2-bedroom, 2.5-bath vacation rental just 2 miles from downtown. With enough space to comfortably sleep 6, this historic 2,000-square-foot abode offers a tastefully furnished interior, private deck,

                                                from $287 / night

                                                $2,004 / week

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                                                Responds fast!
                                                avg. 33 minutes

                                                from $287 / night

                                                Distance approx 13.07 miles from Hampshire County Show on Map

                                                  11

                                                  Conway ski apartment to rent.

                                                  Massachusetts / Conway

                                                  1 3 1 night min

                                                  • 1 bedroom
                                                  • sleeps 3
                                                  • 1 night min
                                                  • Beach/lakeside relaxation
                                                  • Ski
                                                  • Suitable for children age 5+
                                                  Charming one-bedroom apartment situated on 8 beautiful and peaceful acres in the rolling hills of Conway Massachusetts. The apartment has a large kitchen, a sitting room, study "nook", private bath with laundry facilities and a separate entrance. Guests are greeted ev

                                                  from $189 / night

                                                  $1,117 / week

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                                                  from $189 / night

                                                  Distance approx 17.66 miles from Hampshire County Show on Map

                                                    32

                                                    Vacation home rental

                                                    Massachusetts / Springfield

                                                    4 7 100 nights min

                                                    • 4 bedrooms
                                                    • sleeps 7
                                                    • 100 nights min
                                                    • Child friendly
                                                    • Air conditioning
                                                    • Private garden
                                                    Brand New Polished single-family home with 4 bedrooms.! You have the Entire house to yourself. Visit Springfield, Massachusetts where you can stay at this nice, classic authentic, beautiful vacation rental located in the forest park neighborhood, near Massmutual, dow

                                                    from $137 / night

                                                    $954 / week

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                                                    from $137 / night

                                                    Distance approx 15.33 miles from Hampshire County Show on Map

                                                    (1) Excellent 

                                                      13

                                                      Springfield Vacation apartment rental

                                                      Massachusetts / Springfield

                                                      3 6 1 night min

                                                      • 3 bedrooms
                                                      • sleeps 6
                                                      • 1 night min
                                                      • Child friendly
                                                      • Air conditioning
                                                      This beautiful 3 bedroom apartment is located in Old Hill neighborhood, conveniently close to downtown, museums, and colleges. Easy access to highways and public transportation and It is 20 minutes away from Bradley International airport. We welcome everyone. Come and e

                                                      from $90 / night

                                                      $626 / week

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                                                      from $90 / night

                                                      Distance approx 13.64 miles from Hampshire County Show on Map

                                                        8

                                                        Vacation home in Ludlow

                                                        Massachusetts / Ludlow

                                                        4 7 1 night min

                                                        • 4 bedrooms
                                                        • sleeps 7
                                                        • 1 night min
                                                        • Child friendly
                                                        • Air conditioning
                                                        • Private garden
                                                        Beautiful Victorian house with 4 bedrooms set up to accommodate up to 7 Adults House is within a 1/4 mile of Mass Pike entrance, exit 7. Centrally located to the following MGM Casino Basketball Hall of Fame Six Flags Dr. Seuss Museum Mount Holyoke, Smith College, Umass

                                                        from $228 / night

                                                        $1,260 / week

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                                                        from $228 / night

                                                        Distance approx 14.63 miles from Hampshire County Show on Map

                                                          42

                                                          Vacation home in Springfield

                                                          Massachusetts / Springfield

                                                          3 6 1 night min

                                                          • 3 bedrooms
                                                          • sleeps 6
                                                          • 1 night min
                                                          • Child friendly
                                                          • Air conditioning
                                                          • Pet friendly
                                                          This comfortable three bedroom home is located in an excellent neighborhood. Recently renovated, the house has a real homely feel to it. I maintain it well. All in all a great living area, with a fully equipped kitchen, 3 bedrooms with one King, one Queen, one full bed

                                                          from $206 / night

                                                          $1,443 / week

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                                                          Responds fast!
                                                          avg. 38 minutes

                                                          from $206 / night

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