Title: Stockbridge Vacation Rentals from $143: Search Short-Term Rentals | Expedia.com

[Stockbridge Travel Guide](https://expedia.com/Stockbridge.dx162575)[Hotels in Stockbridge](https://expedia.com/Stockbridge-Hotels.d162575.Travel-Guide-Hotels)[Flights to Stockbridge](https://expedia.com/Cheap-Flights-To-Stockbridge.d162575.Travel-Guide-Flights)[Car Rentals in Stockbridge](https://expedia.com/Car-Rentals-In-Stockbridge.d162575.Car-Rental-Guide)[Stockbridge Vacation Packages](https://expedia.com/Stockbridge.d162575.Destination-Travel-Guides)

![autumn in the mountains](https://images.trvl-media.com/place/162575/19bfb038-826c-4b9c-9660-31de551f85b1.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/162575/19bfb038-826c-4b9c-9660-31de551f85b1.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=162575&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=162575&startDate=2026-05-01&endDate=2026-05-03&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 29 - May 31](https://www.expedia.com/Hotel-Search?regionId=162575&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Jun 26 - Jun 28](https://www.expedia.com/Hotel-Search?regionId=162575&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Stockbridge vacation rentals

![Exterior](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/w2439h1242x124y0-c2be86b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/b7940a62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/d970b68c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/78000000/77130000/77128100/77128037/9046d578.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Stockbridge

[](https://www.expedia.com/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information)

10/10

Exceptional

(34 reviews)

"A college friends' retreat was fantastic, in part due to the location, cleanliness and amenities in this 3 bedroom house. Furniture was comfortable and kitchen was stocked with everything we needed. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

cathy c.

$582 nightly

$650 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Stockbridge-Hotels-Walk-Into-Town.h77128037.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/cd7fa5fb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/65ba1b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/a965b40f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Family Bungalow | Living area](https://images.trvl-media.com/lodging/114000000/113780000/113777300/113777287/1e2d02da.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Camping in Williamstown

[](https://www.expedia.com/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information)

9.4/10

Exceptional

(9 reviews)

"Healthy food too!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

GEORGINA

$147 nightly

$165 total

Mar 15 - Mar 16

Total with taxes and fees

[](https://www.expedia.com/Williamstown-Hotels-Huttopia-Berkshires.h113777287.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/aba54efe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/ece507a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/324c211f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/108000000/107110000/107109200/107109194/504a6d5b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mobile Home in Chatham

[](https://www.expedia.com/Chatham-Hotels-Sugar-Shack-300-Square-Feet-Of-Pure-Sweetness.h107109194.Hotel-Information)

10/10

Exceptional

(3 reviews)

"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sue G.

$290 nightly

$327 total

Mar 5 - Mar 6

Total with taxes and fees

[](https://www.expedia.com/Chatham-Hotels-Sugar-Shack-300-Square-Feet-Of-Pure-Sweetness.h107109194.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/db44d375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/9e460e0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby sitting area](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/03675fdd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/2000000/1070000/1066500/1066423/8168a5fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo in Williamstown

[](https://www.expedia.com/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

8.8/10

Excellent

(2,276 reviews)

"Excellent location and terrific space and amenities."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Michelle

$128 nightly

$143 total

Mar 31 - Apr 1

Total with taxes and fees

[](https://www.expedia.com/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

![Daily to-go breakfast for a fee](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/7f42759d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bars/lounges](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/71df138f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/a8f10f60.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/1000000/920000/911400/911313/b35035ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Condo resort in Hancock

[](https://www.expedia.com/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information)

8.2/10

Very Good

(989 reviews)

"nice and clean, good customer service, but the room is smell. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Huang

$149 nightly

$166 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/Hancock-Hotels-Jiminy-Peak-Mountain-Resort.h911313.Hotel-Information)

![Smart TV, books](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/dba15cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/8c55822c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/2281e60c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105230400/105230373/3b9678c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sherwood Forest

[](https://www.expedia.com/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information)

9.8/10

Exceptional

(14 reviews)

"Nicole was very attentive and very quick to respond to any question we had. Her cottage was perfect for a quiet getaway, just what everybody needs!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Matthew F.

$353 nightly

$395 total

Mar 12 - Mar 13

Total with taxes and fees

[](https://www.expedia.com/Becket-Hotels-Dog-Friendly2B1B-In-The-Berkshires-Private-Lake-Community-Whot-Tub-Canoe.h105230373.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/w4000h2662x0y5-f1ed56ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/7d4bb1aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/669a10ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89720000/89714400/89714351/0ab9f2e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Hinsdale

[](https://www.expedia.com/Hinsdale-Hotels-Beautiful-2-Bedroom-Loft-With-Hot-Tub-At-Lake-Ashmere.h89714351.Hotel-Information)

9.8/10

Exceptional

(36 reviews)

"Amazing, peaceful, immaculately clean property. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cec C.

$522 nightly

$583 total

Mar 30 - Mar 31

Total with taxes and fees

[](https://www.expedia.com/Hinsdale-Hotels-Beautiful-2-Bedroom-Loft-With-Hot-Tub-At-Lake-Ashmere.h89714351.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/c0b1b1ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Front of property](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/4d94624e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/c1a3192b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/123000000/122170000/122165500/122165421/4cd10809.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Stephentown

[](https://www.expedia.com/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information)

$499 nightly

$554 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Stephentown-Hotels-8-Mi-To-Jiminy-Peak-Resort-Mtn-View-Home-W-Deck.h122165421.Hotel-Information)

![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/a0f802bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, DVD player](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/a133e616.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/116000000/115470000/115470000/115469906/c729995e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Sherwood Forest

[](https://www.expedia.com/Becket-Hotels-Dog-Friendly-A-Frame-In-The-Berkshires-Walk-To-Lake-With-Beach-Access.h115469906.Hotel-Information)

10/10

Exceptional

(5 reviews)

"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.

$351 nightly

$392 total

Apr 1 - Apr 2

Total with taxes and fees

[](https://www.expedia.com/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/85000000/84680000/84672900/84672833/52bc41a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/caf5dd09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/85000000/84680000/84672900/84672833/6137aab0.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/85000000/84680000/84672900/84672833/c50e9e6c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Great Barrington

[](https://www.expedia.com/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information)

9.8/10

Exceptional

(27 reviews)

"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Cameron M.

$234 nightly

$261 total

Mar 23 - Mar 24

Total with taxes and fees

[](https://www.expedia.com/Great-Barrington-Hotels-Home-In-Great-Barrington.h84672833.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/bae121bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/c5fd4f84.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/0ac89dfb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Indoor pool](https://images.trvl-media.com/lodging/99000000/98520000/98512800/98512708/ffe021cb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

[](https://www.expedia.com/Hancock-Hotels-Must-See-Pirate-Suite-Ski-OnOff-Jiminy-Mtn-View-Fully-Redone-Decor.h98512708.Hotel-Information)

10/10

Exceptional

(5 reviews)

"It was great experience and we loved the ammenities."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Carrie C.

$223 nightly

$249 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Hancock-Hotels-Must-See-Pirate-Suite-Ski-OnOff-Jiminy-Mtn-View-Fully-Redone-Decor.h98512708.Hotel-Information)

![Gift shop](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/2e9623f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/a21be151.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/w1333h900x16y0-bf275b9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/91000000/90790000/90786800/90786767/ced4a56d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

[](https://www.expedia.com/Hancock-Hotels-Must-See-Jurassic-Dino-Suite-At-Jiminy-Country-Inn-Sleeps-4-Ski-OnOff-At-Mtn.h90786767.Hotel-Information)

10/10

Exceptional

(5 reviews)

"We had a great stay! The kids absolutely loved the room. Great location and lots to do. Thanks again!!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jen B.

$220 nightly

$246 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Hancock-Hotels-Must-See-Jurassic-Dino-Suite-At-Jiminy-Country-Inn-Sleeps-4-Ski-OnOff-At-Mtn.h90786767.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/eca50f2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/a764aae5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/51b9c734.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/100000000/99970000/99962400/99962392/d00ad195.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Sheffield

[](https://www.expedia.com/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information)

10/10

Exceptional

(10 reviews)

"Great place. I highly recommend for a group or family. Amazing views! Beautiful property very private and quiet. Cabin was also very well stocked and had great outdoor space. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

deborah d.

$616 nightly

$688 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Sheffield-Hotels-Guesthouse-Cabin-Vacation-Rentals-In-Berkshire-County.h99962392.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/f9227a2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/079bb1c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/3bbdf637.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/120000000/119330000/119322300/119322276/54590b16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Pittsfield

[](https://www.expedia.com/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information)

$277 nightly

$309 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Pittsfield-Hotels-3-Bedroom-House-In-Beautiful-Berkshires.h119322276.Hotel-Information)

![Gift shop](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/2b285fa7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/e60e5176.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/78a1069e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/97000000/96840000/96837300/96837232/w1333h900x16y0-00a84624.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

[](https://www.expedia.com/Gorgeous-Mountain-View-Suite-Ski-OnOff-At-Jiminy-Fully-Redone-Decor.h96837232.Hotel-Information)

10/10

Exceptional

(3 reviews)

"Stayed one night at one of my favorite ski spots. Will be back again!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Neil J.

$220 nightly

$246 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Gorgeous-Mountain-View-Suite-Ski-OnOff-At-Jiminy-Fully-Redone-Decor.h96837232.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/ec2d4d77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/0789534a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/5f67b57c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/125000000/124020000/124014400/124014382/w1008h683x16y0-6785a02b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

[](https://www.expedia.com/Hancock-Hotels-Mountain-Getaway-Suite-Ski-OnOff-Jiminy-Peak-Fully-Redone-Decor.h124014382.Hotel-Information)

10/10

Exceptional

(2 reviews)

"The condo was in good shape with a great location for skiing. Howard was very responsive. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John M.

$220 nightly

$246 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Hancock-Hotels-Mountain-Getaway-Suite-Ski-OnOff-Jiminy-Peak-Fully-Redone-Decor.h124014382.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/121000000/120280000/120275400/120275326/528fbc22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, table tennis, books](https://images.trvl-media.com/lodging/121000000/120280000/120275400/120275326/1c2ae12d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120280000/120275400/120275326/d9eeb6ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/121000000/120280000/120275400/120275326/a296b140.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Becket

[](https://www.expedia.com/Becket-Hotels-Secluded-Sophistication-In-The-Berkshires-49-Acres-Of-Quiet-Luxury-In-Becket.h120275326.Hotel-Information)

10/10

Exceptional

(1 review)

"Beautiful home, attentive host. Location is as peaceful as can be. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Rick M.

$575 nightly

$642 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Becket-Hotels-Secluded-Sophistication-In-The-Berkshires-49-Acres-Of-Quiet-Luxury-In-Becket.h120275326.Hotel-Information)

![TV](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/e3f04cf6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/129a2984.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/dc4b2063.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/93000000/92900000/92899600/92899508/d96d2729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Monterey

[](https://www.expedia.com/Lee-Hotels-Treetop-Hideaway-In-Tyringham.h92899508.Hotel-Information)

9.0/10

Wonderful

(10 reviews)

"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Sarah B.

$526 nightly

$556 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Lee-Hotels-Treetop-Hideaway-In-Tyringham.h92899508.Hotel-Information)

![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111730000/111728400/111728387/d08b3a3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111730000/111728400/111728387/98afb96c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Gift shop](https://images.trvl-media.com/lodging/112000000/111730000/111728400/111728387/bdfc25ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/112000000/111730000/111728400/111728387/7ca07411.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hancock

[](https://www.expedia.com/Hancock-Hotels-Game-Night-Suite-At-Jiminy-Peak-Ski-OnOff-Sleeps-4.h111728387.Hotel-Information)

9.8/10

Exceptional

(7 reviews)

"Great room decorations, travel with two kids they have a great time playing video games"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Andres

$220 nightly

$246 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Hancock-Hotels-Game-Night-Suite-At-Jiminy-Peak-Ski-OnOff-Sleeps-4.h111728387.Hotel-Information)

![](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413821/5daca958.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413821/85f62263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413821/8b4f531c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![](https://images.trvl-media.com/lodging/105000000/104420000/104413900/104413821/2f199563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Hillsdale

[](https://www.expedia.com/Hillsdale-Hotels-The-Brooks-Motel-Exceptional-Suite.h104413821.Hotel-Information)

7.0/10

Good

(4 reviews)

"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

John P.

$179 nightly

$200 total

Mar 4 - Mar 5

Total with taxes and fees

[](https://www.expedia.com/Hillsdale-Hotels-The-Brooks-Motel-Exceptional-Suite.h104413821.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.com/Hotel-Search?startDate=2026-03-17&endDate=2026-03-18&regionId=162575&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Stockbridge%2C+Massachusetts%2C+United+States+of+America&regionId=162575&latLong=42.287586%2C-73.320389&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=CABIN)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Stockbridge%2C+Massachusetts%2C+United+States+of+America&regionId=162575&latLong=42.287586%2C-73.320389&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=VACATION_HOME)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Stockbridge%2C+Massachusetts%2C+United+States+of+America&regionId=162575&latLong=42.287586%2C-73.320389&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=COTTAGE)

Condos

[](https://www.expedia.com/Hotel-Search?destination=Stockbridge%2C+Massachusetts%2C+United+States+of+America&regionId=162575&latLong=42.287586%2C-73.320389&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=CONDO)

Aparthotels

[](https://www.expedia.com/Hotel-Search?destination=Stockbridge%2C+Massachusetts%2C+United+States+of+America&regionId=162575&latLong=42.287586%2C-73.320389&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=APART_HOTEL)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Stockbridge%2C+Massachusetts%2C+United+States+of+America&regionId=162575&latLong=42.287586%2C-73.320389&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=APARTMENT)

Villas

[](https://www.expedia.com/Hotel-Search?destination=Stockbridge%2C+Massachusetts%2C+United+States+of+America&regionId=162575&latLong=42.287586%2C-73.320389&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=VILLA)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Stockbridge%2C+Massachusetts%2C+United+States+of+America&regionId=162575&latLong=42.287586%2C-73.320389&adults=2&startDate=2026-06-01&d1=2026-06-01&endDate=2026-06-04&d2=2026-06-04&lodging=CHALET)

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## Top Stockbridge Hotel Reviews

![Holiday Inn Express Hotel & Suites Great Barrington by IHG](https://images.trvl-media.com/lodging/1000000/900000/892300/892229/eb9d0598_y.jpg)

### Holiday Inn Express Hotel & Suites Great Barrington by IHG

10/10 Excellent

"Simple and clean hotel"

[](https://expedia.com/Great-Barrington-Hotels-Holiday-Inn-Express-Hotel-Suites-Great-Barrington.h892229.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

"Comfortable room with lots of space and easy access to skiing. I needed a baking tray for dinner one night and they were able to provide a baking tray for "

[](https://expedia.com/Williamstown-Hotels-Vacation-Village-In-The-Berkshires.h1066423.Hotel-Information)

![The Yankee, Trademark Collection by Wyndham](https://images.trvl-media.com/lodging/1000000/60000/55000/54944/7b3d704c_y.jpg)

### The Yankee, Trademark Collection by Wyndham

10/10 Excellent

"Room is attractive and clean and the staff is always welcoming. Back rooms, where we stay, are quiet and look out across a marsh to the mountain."

[](https://expedia.com/Lenox-Hotels-Yankee-Inn.h54944.Hotel-Information)

![The Black Swan Lee - Lenox, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/30000/20500/20447/bca96d17_y.jpg)

### The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Room was spotless, staff was very kind!"

[](https://expedia.com/Lee-Hotels-The-Black-Swan-Lee-Lenox.h20447.Hotel-Information)

![Best Western Plus Berkshire Hills Inn & Suites](https://images.trvl-media.com/lodging/1000000/790000/790000/789964/0e628046_y.jpg)

### Best Western Plus Berkshire Hills Inn & Suites

10/10 Excellent

"Clean, friendly staff, quiet, great breakfast, easy to get anywhere locally, updated!"

[](https://expedia.com/Pittsfield-Hotels-Best-Western-Plus-Berkshire-Hills-Inn-Suites.h789964.Hotel-Information)

![Berkshire Mountain Lodge](https://images.trvl-media.com/lodging/12000000/11450000/11449200/11449113/5b83802a_y.jpg)

### Berkshire Mountain Lodge

10/10 Excellent

"Overall pleasant stay; great facilities, staff, and location"

[](https://expedia.com/Pittsfield-Hotels-Berkshire-Mountain-Lodge.h11449113.Hotel-Information)

![Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG](https://images.trvl-media.com/lodging/21000000/20880000/20875100/20875006/98528d27_y.jpg)

### Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

10/10 Excellent

"Very spacious and comfortable. Great for families."

[](https://expedia.com/South-Lee-Hotels-Holiday-Inn-Club-Vacations-Oak-N-Spruce-Resort.h20875006.Hotel-Information)

![The Cornell Inn, Lenox & The Berkshires](https://images.trvl-media.com/lodging/2000000/1640000/1634300/1634230/63812de9_y.jpg)

### The Cornell Inn, Lenox & The Berkshires

10/10 Excellent

"The staff was wonderful "

[](https://expedia.com/Lenox-Hotels-The-Cornell-Inn.h1634230.Hotel-Information)

![Quality Inn Great Barrington](https://images.trvl-media.com/lodging/1000000/130000/128300/128208/ed6ed4e8_y.jpg)

### Quality Inn Great Barrington

10/10 Excellent

"Clean, breakfast was a nice option before heading to Butternut mountain nearby "

[](https://expedia.com/Great-Barrington-Hotels-Days-Inn-By-Wyndham-Great-Barrington.h128208.Hotel-Information)

## Find out more about Stockbridge

**Everything you need to know about Stockbridge vacation rentals**

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Stockbridge vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stockbridge vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

**Stockbridge vacation rentals: An excellent choice for every season**

Whenever you want to travel, a warm welcome awaits you in Stockbridge. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Stockbridge in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $143 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

**How to find incredible deals on Stockbridge rentals**

At Expedia, we put the best Stockbridge vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Stockbridge rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stockbridge vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stockbridge. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

## Explore a world of travel with Expedia

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- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

- [Vacation Homes in Stockbridge ](https://expedia.com/Stockbridge-Private-Vacation-Homes.d162575-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Stockbridge ](https://expedia.com/Stockbridge-Cottages.d162575-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Stockbridge ](https://expedia.com/Stockbridge-Apartments.d162575-aaApartments.Travel-Guide-Accommodation)
- [Condo Rentals in Stockbridge ](https://expedia.com/Stockbridge-Condos.d162575-aaCondos.Travel-Guide-Accommodation)
- [B&B in Stockbridge ](https://expedia.com/Stockbridge-Bed-And-Breakfast.d162575-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Resorts in Stockbridge ](https://expedia.com/Stockbridge-Resorts.d162575-aaResorts.Travel-Guide-Accommodation)
- [Cabin Rentals in Stockbridge ](https://expedia.com/Stockbridge-Cabins.d162575-aaCabins.Travel-Guide-Accommodation)
- [Farmstay in Stockbridge ](https://expedia.com/Stockbridge-Agritourism.d162575-aaAgritourism.Travel-Guide-Accommodation)
- [Motels in Stockbridge ](https://expedia.com/Stockbridge-Motels.d162575-aaMotels.Travel-Guide-Accommodation)
- [Guest Houses in Stockbridge ](https://expedia.com/Stockbridge-Guest-Houses.d162575-aaGuestHouses.Travel-Guide-Accommodation)
- [Aparthotels in Stockbridge ](https://expedia.com/Stockbridge-Apart-Hotels.d162575-aaApartHotels.Travel-Guide-Accommodation)
- [Inns in Stockbridge ](https://expedia.com/Stockbridge-Inns.d162575-aaInns.Travel-Guide-Accommodation)
- [Chalets in Stockbridge ](https://expedia.com/Stockbridge-Chalets.d162575-aaChalets.Travel-Guide-Accommodation)
- [Lodges in Stockbridge ](https://expedia.com/Stockbridge-Lodges.d162575-aaLodges.Travel-Guide-Accommodation)
- [Villas in Stockbridge ](https://expedia.com/Stockbridge-Villas.d162575-aaVillas.Travel-Guide-Accommodation)
- [Condo Resorts in Stockbridge ](https://expedia.com/Stockbridge-Condominium-Resort.d162575-aaCondominiumResort.Travel-Guide-Accommodation)
- [RV Parks in Stockbridge ](https://expedia.com/Stockbridge-RV-Parks.d162575-aaRVParks.Travel-Guide-Accommodation)
- [Country Houses in Stockbridge ](https://expedia.com/Stockbridge-Country-House.d162575-aaCountryHouse.Travel-Guide-Accommodation)
- [Castles in Stockbridge ](https://expedia.com/Stockbridge-Castles.d162575-aaCastles.Travel-Guide-Accommodation)

## Frequently asked questions

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- [Plymouth Hotels](https://expedia.com/Plymouth-Hotels.d9512.Travel-Guide-Hotels)
- [Newburyport Hotels](https://expedia.com/Newburyport-Hotels.d8938.Travel-Guide-Hotels)
- [South Yarmouth Hotels](https://expedia.com/South-Yarmouth-Hotels.d7627.Travel-Guide-Hotels)
- [Lowell Hotels](https://expedia.com/Lowell-Hotels.d8422.Travel-Guide-Hotels)
- [Brockton Hotels](https://expedia.com/Brockton-Hotels.d7068.Travel-Guide-Hotels)
- [Nantucket Hotels](https://expedia.com/Nantucket-Hotels.d285.Travel-Guide-Hotels)
- [Rockport Hotels](https://expedia.com/Rockport-Hotels.d6350.Travel-Guide-Hotels)
- [Northampton Hotels](https://expedia.com/Northampton-Hotels.d9187.Travel-Guide-Hotels)
- [Falmouth Hotels](https://expedia.com/Falmouth-Hotels.d7287.Travel-Guide-Hotels)
- [Worcester Hotels](https://expedia.com/Worcester-Hotels.d6023336.Travel-Guide-Hotels)
- [Marlborough Hotels](https://expedia.com/Marlborough-Hotels.d8869.Travel-Guide-Hotels)
- [Lenox Hotels](https://expedia.com/Lenox-Hotels.d8587.Travel-Guide-Hotels)
- [Gloucester Hotels](https://expedia.com/Gloucester-Hotels.d8008.Travel-Guide-Hotels)
- [New Bedford Hotels](https://expedia.com/New-Bedford-Hotels.d1180.Travel-Guide-Hotels)

Cars

- [Car rentals in Mansfield](https://expedia.com/Car-Rentals-In-Mansfield.d8456.Car-Rental-Guide)
- [Car rentals in Springfield](https://expedia.com/Car-Rentals-In-Springfield.d6047669.Car-Rental-Guide)
- [Car rentals in Worcester](https://expedia.com/Car-Rentals-In-Worcester.d6023336.Car-Rental-Guide)

Activities

- [Things to do in Hyannis](https://expedia.com/Things-To-Do-In-Hyannis.d1544.Travel-Guide-Activities)

Packages

- [Trip to Nantucket](https://expedia.com/Nantucket.d285.Destination-Travel-Guides)

Vacation Rentals

- [Rentals in Nantucket](https://expedia.com/Nantucket-Vacation-Rentals.d285.Travel-Guide-VacationRentals)

General

- [Visit Manchester-by-the-Sea](https://expedia.com/Manchester-By-The-Sea.dx129363)
- [Visit Rockport](https://expedia.com/Rockport.dx6350)

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