Title: Greenfield Vacation Rentals from CA $277: Short-Term Rentals for 2026 | Expedia.ca

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![The Mohawk Trail through The Berkshire Hills (Massachusetts, USA) in autumn](https://images.trvl-media.com/place/8027/451ceee3-7430-40be-a0f3-4fdb2dca05a5.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Greenfield Vacation Rentals

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## Check prices for these dates

Tonight

[Dec 18 - Dec 19](https://www.expedia.ca/Hotel-Search?regionId=8027&startDate=2025-12-18&endDate=2025-12-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Tomorrow

[Dec 19 - Dec 20](https://www.expedia.ca/Hotel-Search?regionId=8027&startDate=2025-12-19&endDate=2025-12-20&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

This weekend

[Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=8027&startDate=2025-12-19&endDate=2025-12-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

Next weekend

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=8027&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Greenfield vacation rentals

![Exterior detail](https://images.trvl-media.com/lodging/121000000/120540000/120530700/120530639/4d1d83e0.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/121000000/120540000/120530700/120530639/7a0cf170.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/121000000/120540000/120530700/120530639/6767fc12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/121000000/120540000/120530700/120530639/721eacf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Greenfield

[](https://www.expedia.ca/Greenfield-Hotels-Charming-Country-Chic-1BR-In-Greenfield-King-Bed.h120530639.Hotel-Information)

8.8/10

Excellent

(3)

"We had an amazing stay! The property was spotless and comfortable. We felt right at home and can’t wait to stay here again! "

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

Garth P.

CA $89

CA $285 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Greenfield-Hotels-Charming-Country-Chic-1BR-In-Greenfield-King-Bed.h120530639.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/79a253e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/70342e8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/01ff54d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/d695e72e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Greenfield

[](https://www.expedia.ca/Greenfield-Hotels-Lovely-2nd-Floor-Apartment.h102386531.Hotel-Information)

10/10

Exceptional

(46)

"Our stay was so amazing. The hosts were wonderul and really adapatable to our family needs."

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

Wendy M.

CA $160

CA $277 total

includes taxes & fees

Dec 19 - Dec 20

[](https://www.expedia.ca/Greenfield-Hotels-Lovely-2nd-Floor-Apartment.h102386531.Hotel-Information)

![Sauna](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/ae82214f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/6cd80eff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/57ed5fc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Sun loungers, beach towels](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/6e3cc5aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Newfane

[](https://www.expedia.ca/Newfane-Hotels-Your-Comprehensive-Wellness-Escape-Sauna-And-Private-Beach.h106418444.Hotel-Information)

10/10

Exceptional

(2)

"The folks are SUPER and made me feel very welome"

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

Mark

CA $186

CA $350 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Newfane-Hotels-Your-Comprehensive-Wellness-Escape-Sauna-And-Private-Beach.h106418444.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/173c3a96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/b0490e8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/9f760421.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/b4e38c32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Whitingham

[](https://www.expedia.ca/Jacksonville-Hotels-Lake-Whitingham-Mount-Snow-Area-Village-Garden-Apartment-2-BR.h108320042.Hotel-Information)

10/10

Exceptional

(1)

"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."

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

Anicia K.

CA $193

CA $421 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Jacksonville-Hotels-Lake-Whitingham-Mount-Snow-Area-Village-Garden-Apartment-2-BR.h108320042.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/a6a78255.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/dfb0d0fe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/f2b8d538.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/52e194b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in East Dover

[](https://www.expedia.ca/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information)

9.8/10

Exceptional

(9)

"Easy to find! Clean! Cozy!! Would definitely stay again! "

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

Roy-michael G.

CA $243

CA $704 total

includes taxes & fees

Jan 7 - Jan 8, 2026

[](https://www.expedia.ca/East-Dover-Hotels-Mandys-Mountain-Chalet-Minutes-From-Mount-Snow.h74683539.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/9832d1e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/6c18250e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/403e3f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/76bef906.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Shelburne Falls

[](https://www.expedia.ca/Shelburne-Falls-Hotels-2-Twin-Beds-On-1st-Floor-With-En-Suite-Bathroom.h120039334.Hotel-Information)

CA $91

CA $207 total

includes taxes & fees

Jan 5 - Jan 6, 2026

[](https://www.expedia.ca/Shelburne-Falls-Hotels-2-Twin-Beds-On-1st-Floor-With-En-Suite-Bathroom.h120039334.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/78692cbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/f112c530.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/3d011b8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113520000/113519100/113519074/1e124241.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Colrain

[](https://www.expedia.ca/Colrain-Hotels-Couples-2-Bedroom-Retreat-Hot-Tub-Air-Hockey-Close-To-ShelburneFalls.h113519074.Hotel-Information)

10/10

Exceptional

(4)

"This place was great! Even though it was raining we enjoyed the hot tub! It was super clean and comfortable. "

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

KayKay S.

[](https://www.expedia.ca/Colrain-Hotels-Couples-2-Bedroom-Retreat-Hot-Tub-Air-Hockey-Close-To-ShelburneFalls.h113519074.Hotel-Information)

![Outdoor spa tub](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/a2eafec2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/163b8b8e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/3a874a87.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/90000000/89680000/89672500/89672463/083f8263.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in West Dover

[](https://www.expedia.ca/West-Dover-Hotels-Hot-Tub.h89672463.Hotel-Information)

10/10

Exceptional

(20)

"Had a delightful time here for the Holiday. Quiet place which held us all comfortably! Easy to get to the places we wanted to go to and was well maintained. Communication with the hosts was fantastic."

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

Jeannine A.

[](https://www.expedia.ca/West-Dover-Hotels-Hot-Tub.h89672463.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112520000/112517100/112517070/d80f7e6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112520000/112517100/112517070/4ef23803.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/113000000/112520000/112517100/112517070/41b13ee0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/113000000/112520000/112517100/112517070/3daf052e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Amherst

[](https://www.expedia.ca/Amherst-Hotels-CLOSE-To-DowntownUMASS-Condo-With-Game-Room-Big-Backyard.h112517070.Hotel-Information)

9.4/10

Exceptional

(18)

"Great property! Thank you for a wonderful stay."

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

David

CA $309

CA $578 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Amherst-Hotels-CLOSE-To-DowntownUMASS-Condo-With-Game-Room-Big-Backyard.h112517070.Hotel-Information)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/a233230f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/41434d0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/7a56f82b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![6 bedrooms, desk, travel crib, WiFi](https://images.trvl-media.com/lodging/93000000/92060000/92050600/92050515/fc7d25b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Whately

[](https://www.expedia.ca/South-Deerfield-Hotels-Cozy-Valley-View-Post-Beam-Villa.h92050515.Hotel-Information)

10/10

Exceptional

(8)

"Thanks for a great stay"

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

Andrea M.

CA $992

CA $1,250 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/South-Deerfield-Hotels-Cozy-Valley-View-Post-Beam-Villa.h92050515.Hotel-Information)

![Interior](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/d9a32dde.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/112000000/111140000/111133500/111133438/16a722ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/17e097bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/ab251044.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Guilford

[](https://www.expedia.ca/Brattleboro-Hotels-Stunning-Glass-House-Nestled-In-The-Vermont-Wilderness.h111133438.Hotel-Information)

10/10

Exceptional

(1)

"The Mirror house was just the perfect place for my wife and I to getaway and reconnect! The house itself was very clean, warm and beautifully decorated. The hot tub, sauna and upstairs “glass room” allowed us to feel as though we were at a spa allowing us to relax and spend time just being together. The natural views and “isolation” helped us to feel like it was just the two of us. This is an ideal place if you are looking to get away with the one you love."

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

Grant D.

CA $347

CA $757 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Brattleboro-Hotels-Stunning-Glass-House-Nestled-In-The-Vermont-Wilderness.h111133438.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/121000000/120420000/120414900/120414848/ec2105a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120420000/120414900/120414848/8031ab01.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/121000000/120420000/120414900/120414848/724bdf50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120420000/120414900/120414848/1f82fc7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Leverett

[](https://www.expedia.ca/Leverett-Hotels-Terrific-3-Bedroom-Unit-In-Charming-Leverett-With-AC.h120414848.Hotel-Information)

10/10

Exceptional

(1)

"The apartment is lovely, so comfortable and quiet!! Caitlin was a wonderful host, very responsive. Would absolutely stay again! "

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

Anna B.

CA $310

CA $639 total

includes taxes & fees

Dec 19 - Dec 20

[](https://www.expedia.ca/Leverett-Hotels-Terrific-3-Bedroom-Unit-In-Charming-Leverett-With-AC.h120414848.Hotel-Information)

![Oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/118000000/117660000/117659900/117659835/f2798a7c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117660000/117659900/117659835/33f72fc4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/118000000/117660000/117659900/117659835/cd5a2739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/118000000/117660000/117659900/117659835/6b7aa883.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Apartment in Northampton

[](https://www.expedia.ca/Northampton-Hotels-Buttons-Modern-Luxury-Walkup-Downtown-Northampton.h117659835.Hotel-Information)

10/10

Exceptional

(2)

"The apartment was very comfortable and had everything we needed for the weekend including nice coffee, cava and a treat. Well equipped kitchen and good bed, towels, storage. Will stay here again"

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

AMY

CA $453

CA $830 total

includes taxes & fees

Jan 6 - Jan 7, 2026

[](https://www.expedia.ca/Northampton-Hotels-Buttons-Modern-Luxury-Walkup-Downtown-Northampton.h117659835.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/6eef057c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/2d0f8d7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/0b026459.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/e32ae717.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet in Guilford

[](https://www.expedia.ca/Brattleboro-Hotels-Vikings-Villages-Resort-Double-Bed-Room.h110890615.Hotel-Information)

CA $379

CA $501 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Brattleboro-Hotels-Vikings-Villages-Resort-Double-Bed-Room.h110890615.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/6ba9f20d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, stereo](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/7ec1e2c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/eca16f90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100730000/100720400/100720354/516bcaba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Whitingham

[](https://www.expedia.ca/Whitingham-Hotels-14mi-To-Mt-Snow-Arcade.h100720354.Hotel-Information)

10/10

Exceptional

(14)

"Extended family of 10 stayed 6 nights and all had a great stay. Beds were comfortable, house was very clean with everything you need to enjoy yourself and was in good repair. "

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

Jacklyn D.

CA $469

CA $939 total

includes taxes & fees

Jan 12 - Jan 13, 2026

[](https://www.expedia.ca/Whitingham-Hotels-14mi-To-Mt-Snow-Arcade.h100720354.Hotel-Information)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/107000000/106260000/106252200/106252146/92b7e91d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/107000000/106260000/106252200/106252146/0ba7e753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/107000000/106260000/106252200/106252146/4777fe6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (3 Bedrooms) | Interior](https://images.trvl-media.com/lodging/107000000/106260000/106252200/106252146/aedc316e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Wilmington

[](https://www.expedia.ca/Wilmington-Hotels-Wilmington-Retreat-Near-Trails.h106252146.Hotel-Information)

10/10

Exceptional

(2)

"Great location and awesome house. Owners were easy to communicate with. "

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

Anonymous traveller

CA $459

CA $1,038 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Wilmington-Hotels-Wilmington-Retreat-Near-Trails.h106252146.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/w1024h593x0y45-2966e99d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/4e9408e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/w1024h490x0y96-4fcb5611.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/92000000/91630000/91621600/91621591/730ec918.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in Charlemont

[](https://www.expedia.ca/Charlemont-Hotels-Bear-Creek-Cabin.h91621591.Hotel-Information)

10/10

Exceptional

(43)

"We enjoyed our stay!!"

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

Hillary S.

CA $550

CA $828 total

includes taxes & fees

Dec 21 - Dec 22

[](https://www.expedia.ca/Charlemont-Hotels-Bear-Creek-Cabin.h91621591.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/101000000/100470000/100466600/100466586/37a48347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/101000000/100470000/100466600/100466586/13543cea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/101000000/100470000/100466600/100466586/6c2b4371.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/101000000/100470000/100466600/100466586/f2f794e6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin in West Dover

[](https://www.expedia.ca/West-Dover-Hotels-Comfy-Ski-Cabin-WHot-Tub.h100466586.Hotel-Information)

10/10

Exceptional

(2)

"It was a sweet and cozy little cottage. Absolutely perfect. Clean, safe and so close to the mountain!! Would absolutely love to stay here again!"

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

Susanne G.

CA $455

CA $979 total

includes taxes & fees

Jan 13 - Jan 14, 2026

[](https://www.expedia.ca/West-Dover-Hotels-Comfy-Ski-Cabin-WHot-Tub.h100466586.Hotel-Information)

![Dining](https://images.trvl-media.com/lodging/113000000/112650000/112644000/112643986/dfb5a38b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/113000000/112650000/112644000/112643986/1cd53f3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/113000000/112650000/112644000/112643986/e110ab89.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/113000000/112650000/112644000/112643986/adc756df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Amherst

[](https://www.expedia.ca/Amherst-Hotels-Luxury-Retreat-InAmherst.h112643986.Hotel-Information)

10/10

Exceptional

(1)

"Very helpful and easy communication. Very clean and nice place. We were very busy and only really were at the place to sleep but it is quiet and perfect for a restful stay."

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

Robert

CA $744

CA $1,155 total

includes taxes & fees

Dec 19 - Dec 20

[](https://www.expedia.ca/Amherst-Hotels-Luxury-Retreat-InAmherst.h112643986.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=2026-01-01&endDate=2026-01-02&regionId=8027&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.ca/Hotel-Search?destination=Greenfield%2C+Massachusetts%2C+United+States+of+America&regionId=8027&latLong=42.587914%2C-72.599411&adults=2&startDate=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=CABIN)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Greenfield%2C+Massachusetts%2C+United+States+of+America&regionId=8027&latLong=42.587914%2C-72.599411&adults=2&startDate=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Greenfield%2C+Massachusetts%2C+United+States+of+America&regionId=8027&latLong=42.587914%2C-72.599411&adults=2&startDate=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Greenfield%2C+Massachusetts%2C+United+States+of+America&regionId=8027&latLong=42.587914%2C-72.599411&adults=2&startDate=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=APARTMENT)

Aparthotels

[](https://www.expedia.ca/Hotel-Search?destination=Greenfield%2C+Massachusetts%2C+United+States+of+America&regionId=8027&latLong=42.587914%2C-72.599411&adults=2&startDate=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=APART_HOTEL)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Greenfield%2C+Massachusetts%2C+United+States+of+America&regionId=8027&latLong=42.587914%2C-72.599411&adults=2&startDate=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=CHALET)

Condos

[](https://www.expedia.ca/Hotel-Search?destination=Greenfield%2C+Massachusetts%2C+United+States+of+America&regionId=8027&latLong=42.587914%2C-72.599411&adults=2&startDate=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=CONDO)

Villas

[](https://www.expedia.ca/Hotel-Search?destination=Greenfield%2C+Massachusetts%2C+United+States+of+America&regionId=8027&latLong=42.587914%2C-72.599411&adults=2&startDate=2026-03-18&d1=2026-03-18&endDate=2026-03-21&d2=2026-03-21&lodging=VILLA)

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## Top Greenfield Hotel Reviews

![The Ellery](https://images.trvl-media.com/lodging/1000000/900000/892700/892654/0b76727c_y.jpg)

### The Ellery

10/10 Excellent

"This is one of my favorite places to stay! I came in late, but you can still make a cup of tea and grab a chocolate chip cookie. It’s quiet, comfortable and immaculate. The continental breakfast has numerous healthy choices and always a selection of baked goods. There is an excellent selection of organic teas and various juices. I’m not a coffee drinker, but I’m sure it’s wonderful as well. "

[](https://expedia.ca/Springfield-Hotels-The-Ellery.h892654.Hotel-Information)

![Inn on Boltwood](https://images.trvl-media.com/lodging/3000000/2030000/2027100/2027065/f10073da_y.jpg)

### Inn on Boltwood

10/10 Excellent

"Check-in was easy and smooth. Friendly staff. Walking in the lobby was like walking into a Hallmark movie. It’s was Christmas time and there were carolers in the beautifully decorated lobby. Nice sized room and bathroom and nicely decorated room. Very convenient location and easy to walk around. "

[](https://expedia.ca/Springfield-Hotels-Inn-On-Boltwood.h2027065.Hotel-Information)

![Comfort Inn & Suites](https://images.trvl-media.com/lodging/1000000/560000/558100/558078/d1319a54_y.jpg)

### Comfort Inn & Suites

10/10 Excellent

"Room cleanliness Friendly front staff Decent breakfast"

[](https://expedia.ca/Springfield-Hotels-Comfort-Inn-Suites.h558078.Hotel-Information)

![The White House Inn](https://images.trvl-media.com/lodging/3000000/2940000/2937400/2937372/fe9c2db1_y.jpg)

### The White House Inn

10/10 Excellent

"There was no hot water the first night.. I let the staff know the next day .. the young man immediately checked room availability and offered 3 options.. he also asked if he could help move us The room was clean. The fireplace was wonderful staff was friendly and accommodating "

[](https://expedia.ca/Wilmington-Hotels-White-House-Inn.h2937372.Hotel-Information)

![Valley Craft Ales](https://images.trvl-media.com/lodging/90000000/89220000/89214100/89214004/c9afe648_y.jpg)

### Valley Craft Ales

10/10 Excellent

"Very easy check in process. They let us know due to it being a pub, it would be loud, but it was very quiet and easy to sleep! The pub area was lovely and had a huge chimney fire for everyone to enjoy and keep warm. The room was clean and well kept! Great experience! "

[](https://expedia.ca/Wilmington-Hotels-Valley-Craft-Ales.h89214004.Hotel-Information)

![Comfort Inn & Suites Brattleboro I-91](https://images.trvl-media.com/lodging/9000000/8790000/8784400/8784377/1032926e_y.jpg)

### Comfort Inn & Suites Brattleboro I-91

10/10 Excellent

"Price, clean and spacious room, comfy bed."

[](https://expedia.ca/Brattleboro-Hotels-Comfort-Inn-Suites-Brattleboro-I-91.h8784377.Hotel-Information)

![Latchis Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/9faca473_y.jpg)

### Latchis Hotel

10/10 Excellent

"Room clean and comfortable "

[](https://expedia.ca/Brattleboro-Hotels-Latchis-Hotel.h1367207.Hotel-Information)

![Hotel UMass](https://images.trvl-media.com/lodging/1000000/490000/480800/480785/4e423f91_y.jpg)

### Hotel UMass

10/10 Excellent

"Love staying on campus when we visit!"

[](https://expedia.ca/Springfield-Hotels-Hotel-UMass.h480785.Hotel-Information)

![Hampton Inn & Suites Greenfield](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/72e137d6_y.jpg)

### Hampton Inn & Suites Greenfield

10/10 Excellent

"Lovely night."

[](https://expedia.ca/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.Hotel-Information)

## Find out more about Greenfield

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Greenfield. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Greenfield ](https://expedia.ca/Greenfield-Private-Vacation-Homes.d8027-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Greenfield ](https://expedia.ca/Greenfield-Cottages.d8027-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Greenfield ](https://expedia.ca/Greenfield-Apartments.d8027-aaApartments.Travel-Guide-Accommodation)
- [Chalets in Greenfield ](https://expedia.ca/Greenfield-Chalets.d8027-aaChalets.Travel-Guide-Accommodation)
- [Cabin Rentals in Greenfield ](https://expedia.ca/Greenfield-Cabins.d8027-aaCabins.Travel-Guide-Accommodation)
- [B&B in Greenfield ](https://expedia.ca/Greenfield-Bed-And-Breakfast.d8027-aaBedAndBreakfast.Travel-Guide-Accommodation)
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- [Condo Rentals in Greenfield ](https://expedia.ca/Greenfield-Condos.d8027-aaCondos.Travel-Guide-Accommodation)
- [Motels in Greenfield ](https://expedia.ca/Greenfield-Motels.d8027-aaMotels.Travel-Guide-Accommodation)
- [Lodges in Greenfield ](https://expedia.ca/Greenfield-Lodges.d8027-aaLodges.Travel-Guide-Accommodation)
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## Frequently asked questions

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