Title: Hampshire County Vacation Home Rentals from CA $206: Search Top Private Vacation Homes for Rent | Expedia.ca [Hampshire County Hotels](https://expedia.ca/Destinations-In-Hampshire-County.d3000443223.Hotel-Destinations)[Vacation Rentals in Hampshire County](https://expedia.ca/Destinations-In-Hampshire-County.d3000443223.Vacation-Rental-Destinations)[Hampshire County Car Rentals](https://expedia.ca/Destinations-In-Hampshire-County.d3000443223.Car-Rental-Destinations)[Hampshire County Vacations](https://expedia.ca/Hampshire-County.d3000443223.Destination-Travel-Guides) ![A6F6E7 AJ9295, Amherst, MA, Massachusetts. Image shot 2001. Exact date unknown.](https://images.trvl-media.com/place/5948/569d230b-3607-47ff-9901-d170437ab921.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Hampshire County Vacation Rentals ## Compare and save - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check prices for these dates In two weeks [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=3000443223&startDate=2026-01-02&endDate=2026-01-04&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=3000443223&startDate=2026-02-13&endDate=2026-02-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=3000443223&startDate=2026-03-13&endDate=2026-03-15&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Apr 10 - Apr 12](https://www.expedia.ca/Hotel-Search?regionId=3000443223&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Cities in Hampshire County ![](https://mediaim.expedia.com/destination/2/8b79416c267c66a0fe7820cb30d71155.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Amherst [](https://expedia.ca/Amherst-Private-Vacation-Homes.d5948-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/62e8fd70ba8b07a5665a19f5becce243.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Northampton [](https://expedia.ca/Northampton-Private-Vacation-Homes.d9187-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/429e802d31ae1701bd60611bd011435a.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### South Hadley [](https://expedia.ca/South-Hadley-Private-Vacation-Homes.d6747-aaPrivateVacationHomes.Travel-Guide-Accommodation) ![](https://mediaim.expedia.com/destination/2/1c480d69ccad89b23bddcbee4c3f5644.jpg?impolicy=fcrop&w=384&h=216&q=medium) #### Hadley [](https://expedia.ca/Hadley-Private-Vacation-Homes.d11961-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Our top choices for Hampshire County vacation homes ![Dining](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/458d1d2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/w2988h3984x23y25-6b991349.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![5 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/aef5544c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/eb8c4f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Colrain [](https://www.expedia.ca/Colrain-Hotels-10-Guests-5-BR.h37817199.Hotel-Information) 9.8/10 Exceptional (38) "Great house for family gatherings " ![United Kingdom](https://a.travel-assets.com/egds/marks/flags/uk.svg) John Paul B. CA $411 CA $908 total includes taxes & fees Dec 19 - Dec 20 [](https://www.expedia.ca/Colrain-Hotels-10-Guests-5-BR.h37817199.Hotel-Information) ![Game room](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/406cc767.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Microwave, oven, stovetop, eco-friendly cleaning products](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/780d89c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/862ec0e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/121000000/120310000/120304900/120304823/59edf6fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Great Barrington [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) 9.4/10 Exceptional (6) CA $279 CA $406 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Great-Barrington-Hotels-Cozy-Riverfront-Escape-In-Great-Barrington-Whiskers-On-The-Water.h120304823.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/118000000/117240000/117235800/117235714/w1079h810x0y1-a5b49680.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/118000000/117240000/117235800/117235714/w1048h809x0y1-404bd42a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117240000/117235800/117235714/c94d091e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/118000000/117240000/117235800/117235714/73ba4c3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Ludlow [](https://www.expedia.ca/Ludlow-Hotels-Tiny-Home-With-AC-And-WiFi-In-Lovely-Ludlow.h117235714.Hotel-Information) 8.4/10 Very good (9) "Good stay for an overnight in the area, location was a little tricky to find at night but once I did it was easy to get in. Had all the amenities needed for a short stay and is near the highway for quick on and off." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew H. CA $109 CA $206 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Ludlow-Hotels-Tiny-Home-With-AC-And-WiFi-In-Lovely-Ludlow.h117235714.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/63595554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/62b3ce52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/eccd60b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/34000000/33940000/33932800/33932760/7d7a19ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Stockbridge [](https://www.expedia.ca/West-Stockbridge-Hotels-Location-Location-Berkshire-Glamour.h33932760.Hotel-Information) 10/10 Exceptional (135) "Clean house, well appointed, great location, responsive owner" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) sara m. [](https://www.expedia.ca/West-Stockbridge-Hotels-Location-Location-Berkshire-Glamour.h33932760.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/122000000/121220000/121211000/121210927/486f914e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/122000000/121220000/121211000/121210927/83beab49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/122000000/121220000/121211000/121210927/c2e5501a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121220000/121211000/121210927/b5fe1e13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Goshen [](https://www.expedia.ca/Goshen-Hotels-Experience-Three-Sisters-Sanctuary-In-Goshen.h121210927.Hotel-Information) 10/10 Exceptional (2) "We had such a great time staying here as always. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David F. [](https://www.expedia.ca/Goshen-Hotels-Experience-Three-Sisters-Sanctuary-In-Goshen.h121210927.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/96000000/95210000/95207600/95207502/fb316035.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/96000000/95210000/95207600/95207502/1359a0ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/96000000/95210000/95207600/95207502/4d8d7aea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/96000000/95210000/95207600/95207502/0a528814.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lanesborough [](https://www.expedia.ca/Lanesborough-Hotels-Cozy-Lake-House-With-Hot-Tub-Enjoy-Everything-The-Berkshires-Have-To-Offer.h95207502.Hotel-Information) 10/10 Exceptional (8) "Everything was just as advertised and we really enjoyed the view and the hot tub. Perfect spot for a quick getaway! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cindy B. [](https://www.expedia.ca/Lanesborough-Hotels-Cozy-Lake-House-With-Hot-Tub-Enjoy-Everything-The-Berkshires-Have-To-Offer.h95207502.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/afd0b229.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/bc016b9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/2598e461.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/31000000/30780000/30777100/30777071/f26456ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Sherwood Forest [](https://www.expedia.ca/Becket-Hotels-Peace-And-Quiet-On-The-Lake.h30777071.Hotel-Information) 9.6/10 Exceptional (230) "Great communication, comfortable home, love the location" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Susan C. [](https://www.expedia.ca/Becket-Hotels-Peace-And-Quiet-On-The-Lake.h30777071.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/a5ddb496.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/85b23873.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/63cb703a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, video games, DVD player](https://images.trvl-media.com/lodging/34000000/33500000/33492300/33492239/89102e9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Pittsfield [](https://www.expedia.ca/Pittsfield-Hotels-Beautiful-8-Bedroom.h33492239.Hotel-Information) 9.8/10 Exceptional (150) "We had a fabulous stay at this lovely home in the Berkshires! The house was well equipped with everything needed to make our stay with our family so enjoyable. Great communication with the host in helping to resolve a small issue with loss of power on 2nd floor but was easily resolved." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sarah A. [](https://www.expedia.ca/Pittsfield-Hotels-Beautiful-8-Bedroom.h33492239.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/65000000/64150000/64145900/64145854/3d8d954d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/65000000/64150000/64145900/64145854/4034ab20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/65000000/64150000/64145900/64145854/1e9190a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/65000000/64150000/64145900/64145854/3e04c670.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lanesborough [](https://www.expedia.ca/Lanesborough-Hotels-Wildlife-Cottage-By-The-Lake.h64145854.Hotel-Information) 9.6/10 Exceptional (74) "This house is immaculate. Loved the fire pit and the jacuzzi. Very comfortable house. We spent quite a bit of time relaxing on the deck of the living room. We did get a bit lost getting there, but the caretaker, Jill, was readily available and not only helped us with directions, but gave us suggestions on where to go for groceries, etc. Very friendly and helpful woman. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Barbara A. [](https://www.expedia.ca/Lanesborough-Hotels-Wildlife-Cottage-By-The-Lake.h64145854.Hotel-Information) ![Dining](https://images.trvl-media.com/lodging/102000000/101280000/101271300/101271254/f8fd77b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/102000000/101280000/101271300/101271254/36d358fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, foosball](https://images.trvl-media.com/lodging/102000000/101280000/101271300/101271254/8b9796c0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/102000000/101280000/101271300/101271254/2267bfa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lee [](https://www.expedia.ca/Lee-Hotels-Cordelia-By-AvantStay-Amazing-Backyard.h101271254.Hotel-Information) 9.6/10 Exceptional (19) "Great communication, perfect location for everything we wanted to do that weekend and a beautiful home! We used the indoor and outdoor spaces and had a wonderful time!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie L. [](https://www.expedia.ca/Lee-Hotels-Cordelia-By-AvantStay-Amazing-Backyard.h101271254.Hotel-Information) ![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/104000000/103770000/103762600/103762537/5c7a7785.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/104000000/103770000/103762600/103762537/79e0691c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/104000000/103770000/103762600/103762537/e86b918e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/104000000/103770000/103762600/103762537/84a6c953.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in South End [](https://www.expedia.ca/Springfield-Hotels-Updated-3Bedroom-5beds-Group-ReadyWalk-To-The-Casino-And-Play-Game-Of-Pool.h103762537.Hotel-Information) 9.0/10 Wonderful (2) "Beautifully renovated and easy travels to many family and adult attractions locally. Parking is street side and we never had an issue parking our 2 vehicles out front of the home." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Molly S. [](https://www.expedia.ca/Springfield-Hotels-Updated-3Bedroom-5beds-Group-ReadyWalk-To-The-Casino-And-Play-Game-Of-Pool.h103762537.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/f305b62e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/d80b29aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private kitchen](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/037efde9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/121000000/120470000/120461900/120461825/76291106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Charlemont [](https://www.expedia.ca/Charlemont-Hotels-Riverbend-Berkshire-East-Basecamp-3-Bedrooms-Available.h120461825.Hotel-Information) CA $220 CA $585 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Charlemont-Hotels-Riverbend-Berkshire-East-Basecamp-3-Bedrooms-Available.h120461825.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/108000000/107610000/107605300/107605272/3eafff6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/108000000/107610000/107605300/107605272/7474f837.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/108000000/107610000/107605300/107605272/6d7743ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/108000000/107610000/107605300/107605272/6251f7f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Shelburne Falls [](https://www.expedia.ca/Shelburne-Falls-Hotels-Stylish-New-2-Bedroom-Property-In-Enchanting-Shelburne-Falls-Village.h107605272.Hotel-Information) 10/10 Exceptional (20) "Great place to stay ,close to town.Very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Hope D. [](https://www.expedia.ca/Shelburne-Falls-Hotels-Stylish-New-2-Bedroom-Property-In-Enchanting-Shelburne-Falls-Village.h107605272.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102040000/102036900/102036815/9492003f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/103000000/102040000/102036900/102036815/05c29f4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV, fireplace](https://images.trvl-media.com/lodging/103000000/102040000/102036900/102036815/w981h960x0y0-dffb4572.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/103000000/102040000/102036900/102036815/6eea85ca.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lee [](https://www.expedia.ca/Lee-Hotels-Lee-Manor-For-Lasting-Memories.h102036815.Hotel-Information) 10/10 Exceptional (21) "Wonderful stay, beautiful, well equipped and clean property. Highly recommend for an adult famiky getaway " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) jennifer r. [](https://www.expedia.ca/Lee-Hotels-Lee-Manor-For-Lasting-Memories.h102036815.Hotel-Information) ![Smart TV, fireplace, video games, books](https://images.trvl-media.com/lodging/32000000/31100000/31095400/31095318/62c9be07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/32000000/31100000/31095400/31095318/e8a78bfc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/32000000/31100000/31095400/31095318/b12618d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/32000000/31100000/31095400/31095318/cda1802b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Forest Park [](https://www.expedia.ca/Springfield-Hotels-Upscaled-Home-In-A-Quiet-Neighborhood-You-Have-The-Entire-Home-To-Yourself.h31095318.Hotel-Information) 9.8/10 Exceptional (36) "His home was great. It had everything our group needed and was as advertised. We enjoyed our stay and would definitely come back again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Matthew C. CA $242 CA $415 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Springfield-Hotels-Upscaled-Home-In-A-Quiet-Neighborhood-You-Have-The-Entire-Home-To-Yourself.h31095318.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/02c7301e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/a366bf74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/960bf7a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/92000000/91600000/91593500/91593496/b2d17216.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Lenox [](https://www.expedia.ca/Lenox-Hotels-October-Mountain-Escape.h91593496.Hotel-Information) 9.2/10 Wonderful (33) "Beautiful property. The house and grounds, including a beautiful pool were amazing. Loved sitting on the porch and watching the birds.So much to do in the Berkshires, would definitely like to come back." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jacquie S. [](https://www.expedia.ca/Lenox-Hotels-October-Mountain-Escape.h91593496.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/75000000/74630000/74627300/74627282/12940d97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74630000/74627300/74627282/763a1877.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/75000000/74630000/74627300/74627282/48347ecd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/75000000/74630000/74627300/74627282/c4be44f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Whitingham [](https://www.expedia.ca/Whitingham-Hotels-Cozy-Lakeside-Tiny-Home.h74627282.Hotel-Information) 10/10 Exceptional (50) "Great stay perfect for 2 people, relax on then porch and look at the lake! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Keith D. [](https://www.expedia.ca/Whitingham-Hotels-Cozy-Lakeside-Tiny-Home.h74627282.Hotel-Information) ![TV](https://images.trvl-media.com/lodging/109000000/108030000/108027600/108027600/d21acdd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/109000000/108030000/108027600/108027600/9731709b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108030000/108027600/108027600/62c073e3_edited_06ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Game room](https://images.trvl-media.com/lodging/109000000/108030000/108027600/108027600/682a8ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Pine Point [](https://www.expedia.ca/Springfield-Hotels-3-Bedroom-House-In-Perfect-Springfield-With-WiFi.h108027600.Hotel-Information) 9.6/10 Exceptional (7) "The whole experience was great. The host was very nice and the place is comfy and enjoyable to stay at. Highly recommend. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joel K. [](https://www.expedia.ca/Springfield-Hotels-3-Bedroom-House-In-Perfect-Springfield-With-WiFi.h108027600.Hotel-Information) ![Outdoor dining](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/ecdea449.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/83d3f833_edited_d758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/51a25809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/4bbc4f9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Sherwood Forest [](https://www.expedia.ca/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information) 10/10 Exceptional (5) "We loved it! Lots of local hiking trails and a wonderful relaxing place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Sharon K. CA $201 CA $514 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33970000/33960400/33960335/222fc9b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![6 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/34000000/33970000/33960400/33960335/10587e2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/34000000/33970000/33960400/33960335/fbda7092.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/34000000/33970000/33960400/33960335/9a679a9c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vacation Home in Stockbridge [](https://www.expedia.ca/Stockbridge-Hotels-A-Grand-Estate-In-Historic-Stockbridge.h33960335.Hotel-Information) 10/10 Exceptional (104) "Great house with gracious and responsive hosts. Everything in working order and the houseclean and grand." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David H. [](https://www.expedia.ca/Stockbridge-Hotels-A-Grand-Estate-In-Historic-Stockbridge.h33960335.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-12-31&endDate=2026-01-01®ionId=3000443223&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FHampshire-County-Private-Vacation-Homes.d3000443223-aaPrivateVacationHomes.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FHampshire-County-Private-Vacation-Homes.d3000443223-aaPrivateVacationHomes.Travel-Guide-Accommodation) ## Top Hampshire County Hotel Reviews ![Hampton Inn Springfield South Enfield](https://images.trvl-media.com/lodging/3000000/2360000/2351500/2351481/1e4caef0_y.jpg) ### Hampton Inn Springfield South Enfield 10/10 Excellent "The Hampton Inn in Enfield was absolutely wonderful! Friendly staff \~ everyone we met! Excellent breakfast buffet. Clean, well-appointed room. Very, very nice place to stay. I highly recommend it!" [](https://expedia.ca/Hartford-Hotels-Hampton-Inn-Springfield-South-Enfield.h2351481.Hotel-Information) ![Days Inn by Wyndham Windsor Locks / Bradley Intl Airport](https://images.trvl-media.com/lodging/1000000/20000/17600/17518/1117a9b1_y.jpg) ### Days Inn by Wyndham Windsor Locks / Bradley Intl Airport 10/10 Excellent "Great place great people redone rooms" [](https://expedia.ca/Hartford-Hotels-Days-Inn-By-Wyndham-Windsor-Locks-Bradley-Intl-Airport.h17518.Hotel-Information) ![MGM Springfield](https://images.trvl-media.com/lodging/28000000/27670000/27664900/27664860/c76c1f43_y.jpg) ### MGM Springfield 10/10 Excellent "Coffee shops mediocre. Consider getting Starbucks? Great overall " [](https://expedia.ca/Springfield-Hotels-MGM-Springfield.h27664860.Hotel-Information) ![Holiday Inn Express Springfield Downtown by IHG](https://images.trvl-media.com/lodging/19000000/18110000/18101700/18101636/4d56c1cb_y.jpg) ### Holiday Inn Express Springfield Downtown by IHG 10/10 Excellent "The room was awesome with room to walk around, it was very clean and the bathroom was roomy and very nice. Breakfast was very good also 😊👍 " [](https://expedia.ca/Springfield-Hotels-Holiday-Inn-Express-Springfield-Downtown.h18101636.Hotel-Information) ![Sheraton Hartford Hotel at Bradley Airport](https://images.trvl-media.com/lodging/1000000/10000/4700/4632/c8edc11d_y.jpg) ### Sheraton Hartford Hotel at Bradley Airport 10/10 Excellent "Room is clean staff is friendly. Checkin was easy" [](https://expedia.ca/Hartford-Hotels-Sheraton-Hartford-Hotel-At-Bradley-Airport.h4632.Hotel-Information) ![Vacation Village in the Berkshires](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/012d1fc0_y.jpg) ### Vacation Village in the Berkshires 10/10 Excellent "Awesome for ski" [](https://expedia.ca/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information) ![D. Hotel Suites & Spa](https://images.trvl-media.com/lodging/1000000/850000/849400/849303/5f3c4e34_y.jpg) ### D. Hotel Suites & Spa 10/10 Excellent "Great staff." [](https://expedia.ca/Springfield-Hotels-D-Hotel-Suites-Spa.h849303.Hotel-Information) ![Motel 6 Enfield, CT - Hartford](https://images.trvl-media.com/lodging/1000000/1000000/996200/996142/b47af559_y.jpg) ### Motel 6 Enfield, CT - Hartford 10/10 Excellent "Perfect " [](https://expedia.ca/Hartford-Hotels-Motel-6-Enfield.h996142.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport](https://images.trvl-media.com/lodging/1000000/50000/50000/49978/13428cf5_y.jpg) ### La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport 10/10 Excellent "Free Wi-Fi was very slow. You have to pay $4.95 per day for fast Wi-Fi. That was disappointing." [](https://expedia.ca/Hartford-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Hartford-Bradley-Airport.h49978.Hotel-Information) ## Find out more about Hampshire County ## Hampshire County Vacation Homes information | Number of reviews | 896 | | ----------------- | ------------------ | | Accommodation | 489 Vacation Homes | | Lowest Price | CA $206 | | Highest Price | CA $908 | ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [Hotels near Academy of Music Theater ](https://www.expedia.ca/Academy-Of-Music-Theater-Hotels.0-l6070271-0.Travel-Guide-Filter-Hotels) - [Hotels near Amherst Golf Course ](https://www.expedia.ca/Amherst-Golf-Course-Hotels.0-l553248621563221012-0.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Amherst ](https://www.expedia.ca/Amherst-Hotels-Beach-Hotel.0-0-d5948-tBeachHotel.Travel-Guide-Filter-Hotels) - [Best Western Hotels in Amherst ](https://www.expedia.ca/Amherst-Hotels-Best-Western.0-0-d5948--bBestWestern.Travel-Guide-Filter-Hotels) - 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