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

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![Winchester, New Hampshire in winter ](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

![](https://images.trvl-media.com/place/3000447144/3e6a6279-072b-4adb-98ce-884d4d6659f9.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

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## Check prices for these dates

In two weeks

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-04-03&endDate=2026-04-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[May 1 - May 3](https://www.expedia.ca/Hotel-Search?regionId=3000447144&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 four months

[May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=3000447144&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)

## Our top choices for Winchester vacation rentals

![Exterior](https://images.trvl-media.com/lodging/126000000/125300000/125300000/125299924/f2b21706.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/126000000/125300000/125300000/125299924/5d550d48.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/126000000/125300000/125300000/125299924/88c9bc33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, free WiFi](https://images.trvl-media.com/lodging/126000000/125300000/125300000/125299924/bf758959.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy & Bright Guest Suite

[](https://www.expedia.ca/Peterborough-Hotels-Cozy-Bright-Guest-Suite.h125299924.Hotel-Information)

Peterborough

CA $109

CA $261 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Peterborough-Hotels-Cozy-Bright-Guest-Suite.h125299924.Hotel-Information)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/9b2c42ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/89a0b30d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/ad9f4a52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/18e29612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

[](https://www.expedia.ca/Rindge-Hotels-2-Bed.h88302089.Hotel-Information)

Rindge

10/10

Exceptional

(23 reviews)

"The cottage was a great place to stay. Very conveniently located to where we wanted to travel to. It has a great view of the lake, very clean and comfortable."

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

Nicole B.

CA $209

CA $470 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Rindge-Hotels-2-Bed.h88302089.Hotel-Information)

![Private kitchen](https://images.trvl-media.com/lodging/124000000/123530000/123526000/123525991/5805ee12.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/124000000/123530000/123526000/123525991/68a2c1c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/124000000/123530000/123526000/123525991/4de5a1d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/124000000/123530000/123526000/123525991/648bcca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Studio with a View. Bring your dog, too!

[](https://www.expedia.ca/Brattleboro-Hotels-The-Studio-With-A-View-Bring-Your-Dog.h123525991.Hotel-Information)

Brattleboro

10/10

Exceptional

(2 reviews)

"Great cozy little mountain cabin stay!! Well-appointed studio barn/cabin with scenic view and great proximity to skiing. Would stay again : )"

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

James M.

[](https://www.expedia.ca/Brattleboro-Hotels-The-Studio-With-A-View-Bring-Your-Dog.h123525991.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/fb54d968.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/06a81bab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/57c0c927.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/e861780f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

[](https://www.expedia.ca/Peterborough-Hotels-Studio-Apt-With-Full-Kitchen-1-Minute-Stroll-Over-Picturesque-Bridge-Into-Town.h102238328.Hotel-Information)

Peterborough

9.8/10

Exceptional

(31 reviews)

"Fully equipped kitchen, comfortable open floor plan, easy walk to downtown and very hospitable—thank you—we’d like to stay here again next year!"

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

Mark

CA $80

CA $191 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Peterborough-Hotels-Studio-Apt-With-Full-Kitchen-1-Minute-Stroll-Over-Picturesque-Bridge-Into-Town.h102238328.Hotel-Information)

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

![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/7e27ff2e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, offices](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/c8db5a9a.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)

### Lovely 2nd Floor Apartment

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

Greenfield

10/10

Exceptional

(48 reviews)

"Very cute apartment, clean and nice furnishings, bed was very comfortable."

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

Matthew H.

CA $159

CA $277 total

includes taxes & fees

Feb 10 - Feb 11

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

![Interior](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/262afaed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/d458659b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/75d33052.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/c9f7c522.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cozy apt in beautiful secluded spot 15 mins from Mt Snow

[](https://www.expedia.ca/East-Dover-Hotels-Cozy-Apt-In-Beautiful-Secluded-Spot-15-Mins-From-Mt-Snow.h113155266.Hotel-Information)

Dover

10/10

Exceptional

(4 reviews)

"Cozy little spot that had everything we needed. Peaceful, quiet, and once the rain let up on our stay we walked out to the gorgeous little pond on the property. So serene. Catherine was great!"

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

Erica H.

CA $116

CA $280 total

includes taxes & fees

Feb 28 - Mar 1

[](https://www.expedia.ca/East-Dover-Hotels-Cozy-Apt-In-Beautiful-Secluded-Spot-15-Mins-From-Mt-Snow.h113155266.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/25e52beb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/9396f37e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/450474c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/c6092f96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Finnish Cabin with Sauna on Lake Monomonac

[](https://www.expedia.ca/Rindge-Hotels-Finnish-Cabin-With-Sauna-On-Lake-Monomonac.h106476934.Hotel-Information)

Rindge

10/10

Exceptional

(11 reviews)

"Amazing place. We really enjoyed our brief stay. Great host. "

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

Gary S.

CA $207

CA $405 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Rindge-Hotels-Finnish-Cabin-With-Sauna-On-Lake-Monomonac.h106476934.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/56fde17e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/303ca4c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lobby](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/920497ef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/57a1a4c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Grey Cabin with Sauna on Lake Monomonac

[](https://www.expedia.ca/Rindge-Hotels-Grey-Cabin-With-Sauna-On-Lake-Monomonac.h106489950.Hotel-Information)

Rindge

7.6/10

Good

(4 reviews)

"Great location host was on it.anything u needed he was there.no ac was the only thing.but it was unusally hot.i would go again"

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

Brian

CA $233

CA $479 total

includes taxes & fees

Feb 22 - Feb 23

[](https://www.expedia.ca/Rindge-Hotels-Grey-Cabin-With-Sauna-On-Lake-Monomonac.h106489950.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/3696f739.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/1fd17ad6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/0545aa58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/d2180d1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Beautiful Adirondack Cabin with Sauna on Lake Monomonac

[](https://www.expedia.ca/Rindge-Hotels-Beautiful-Adirondack-Cabin-With-Sauna-On-Lake-Monomonac.h106335693.Hotel-Information)

Rindge

9.8/10

Exceptional

(25 reviews)

"This is a great property, and Jim is a wonderful host. He accommodated all our requests for sauna use and provided helpful tips about the area. We hope to return again one day!"

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

Leigh C.

CA $259

CA $512 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Rindge-Hotels-Beautiful-Adirondack-Cabin-With-Sauna-On-Lake-Monomonac.h106335693.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/ab38fefa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

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

![Interior](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/7eb92a36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/07d1d9b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vikings Villages Resort - Double Bed Room

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

Guilford

CA $239

CA $294 total

includes taxes & fees

Feb 10 - Feb 11

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

![Outdoor spa tub](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/019323ac.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/ee17c612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/31e9eac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/b4c71f0d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Modern Downtown 12ppl Hot Tub Fire Pit Games

[](https://www.expedia.ca/Keene-Hotels-Downtown-Hot-Tub-Escape.h97317603.Hotel-Information)

Keene

9.6/10

Exceptional

(22 reviews)

"Good location for some event staff to stay while we were hosting a conference in town. Simple check-in/out. Would rent again."

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

Jack P.

CA $212

CA $430 total

includes taxes & fees

Feb 26 - Feb 27

[](https://www.expedia.ca/Keene-Hotels-Downtown-Hot-Tub-Escape.h97317603.Hotel-Information)

![Living area](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/9530dfe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/40c2e2d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/112000000/111140000/111133500/111133438/962a1a2a.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)

### Stunning Glass House nestled in the Vermont wilderness!

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

Guilford

10/10

Exceptional

(1 review)

"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 $181

CA $562 total

includes taxes & fees

Feb 11 - Feb 12

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

![Property grounds](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/b3ddab44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/75000000/74690000/74683600/74683539/bcfc0861.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/75000000/74690000/74683600/74683539/1ce3fb4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Chalet Mount Snow/Stratton Skiing/hiking

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

East Dover

9.8/10

Exceptional

(10 reviews)

"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 $210

CA $665 total

includes taxes & fees

Mar 2 - Mar 3

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

![Property grounds](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/1ec609e9.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)

![Outdoor dining](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/5e42b791.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/0997d6b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lake Whitingham & Mount Snow Area Village Apartment

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

Whitingham

10/10

Exceptional

(1 review)

"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 $191

CA $421 total

includes taxes & fees

Feb 10 - Feb 11

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

![WiFi, bed sheets](https://images.trvl-media.com/lodging/125000000/124220000/124215600/124215586/a7ea3011.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/125000000/124220000/124215600/124215586/ed45b7cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/125000000/124220000/124215600/124215586/9ef8fd65.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, fireplace](https://images.trvl-media.com/lodging/125000000/124220000/124215600/124215586/f7a202b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious lakeside 4-bedroom house in beautiful Ashburnham

[](https://www.expedia.ca/Winchendon-Hotels-Spacious-Lakeside-4-Bedroom-House-In-Beautiful-Ashburnham.h124215586.Hotel-Information)

Ashburnham

CA $274

CA $493 total

includes taxes & fees

Feb 11 - Feb 12

[](https://www.expedia.ca/Winchendon-Hotels-Spacious-Lakeside-4-Bedroom-House-In-Beautiful-Ashburnham.h124215586.Hotel-Information)

![TV, books](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/8f769c56.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Shower, eco-friendly toiletries, hair dryer](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/17c13c0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/d16d9700.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/8d64a97b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

[](https://www.expedia.ca/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.Hotel-Information)

Walpole

10/10

Exceptional

(8 reviews)

"Beautiful cozy cottage. Very clean. Wonderful host."

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

Gloria A.

CA $280

CA $344 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/121000000/120420000/120414900/120414848/4f40d5b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![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/121000000/120420000/120414900/120414848/1f82fc7d.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)

### Terrific 3-bedroom unit in charming Leverett with AC

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

Leverett

10/10

Exceptional

(1 review)

"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 $308

CA $652 total

includes taxes & fees

Feb 10 - Feb 11

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

![Exterior](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/fe04814b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/a1a0916f.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)

![Smart TV, fireplace](https://images.trvl-media.com/lodging/90000000/89680000/89672500/89672463/f1c572ee.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 8 Minutes to ski Mount Snow, Hot Tub, Game Room, Fire Pit, Dog friendly

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

West Dover

10/10

Exceptional

(23 reviews)

"Wonderful time..the home was very spacious and comfortable..great location!"

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

Ellen P.

CA $401

CA $1,048 total

includes taxes & fees

Feb 10 - Feb 11

[](https://www.expedia.ca/West-Dover-Hotels-Hot-Tub.h89672463.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/d986e55d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039334/6d3522c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 Twin beds on 1st floor with En-suite bathroom.

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

Shelburne Falls

CA $126

CA $246 total

includes taxes & fees

Mar 3 - Mar 4

[](https://www.expedia.ca/Shelburne-Falls-Hotels-2-Twin-Beds-On-1st-Floor-With-En-Suite-Bathroom.h120039334.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=2026-02-23&endDate=2026-02-24&regionId=3000447144&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=Winchester%2C+New+Hampshire%2C+United+States+of+America&regionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=CABIN)

Cottages

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Private vacation homes

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America&regionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America&regionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=APARTMENT)

Chalets

[](https://www.expedia.ca/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America&regionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-05-09&d1=2026-05-09&endDate=2026-05-12&d2=2026-05-12&lodging=CHALET)

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## Top Winchester Hotel Reviews

![Four Columns Inn](https://images.trvl-media.com/lodging/84000000/83260000/83257800/83257793/be42824d_y.jpg)

### Four Columns Inn

10/10 Excellent

"We stayed in the John Fane room which is in the main building. It is cute as a button. Perfect for couples. "

[](https://expedia.ca/Newfane-Hotels-Four-Columns-Inn.h83257793.Hotel-Information)

![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/43775dcc_y.jpg)

### The Putney Inn

10/10 Excellent

"For the money it was very decent in the clerk was nice also"

[](https://expedia.ca/Putney-Hotels-The-Putney-Inn.h1810866.Hotel-Information)

![Vikings Villages Resort](https://images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/6c062779_y.jpg)

### Vikings Villages Resort

10/10 Excellent

"My husband and I really don’t know where to begin about this place. It was just absolutely fantastic. In every way. The entire facility is a work of art.!!!!! "

[](https://expedia.ca/Brattleboro-Hotels-Vikings-Villages.h92078509.Hotel-Information)

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

### Latchis Hotel

10/10 Excellent

"Spotless room -- all the basics. Friendly & helpful staff"

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

![Holiday Inn Express Hotel & Suites Brattleboro by IHG](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/b5010c60_y.jpg)

### Holiday Inn Express Hotel & Suites Brattleboro by IHG

10/10 Excellent

"The staff, amenities and room were a high standard. Although we only stayed one night we had everything we needed to be comfortable and cozy "

[](https://expedia.ca/Brattleboro-Hotels-Holiday-Inn-Express-Hotel-Suites-Brattleboro.h845427.Hotel-Information)

![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/a903e42a_y.jpg)

### Colonial Motel And Spa

10/10 Excellent

"Amenities were great!"

[](https://expedia.ca/Brattleboro-Hotels-Colonial-Motel-And-Spa.h1070729.Hotel-Information)

![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/214f3dc0_y.jpg)

### The Covered Bridge Inn

10/10 Excellent

"Good"

[](https://expedia.ca/Brattleboro-Hotels-The-Covered-Bridge-Inn.h27661353.Hotel-Information)

![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/e0570769_y.jpg)

### The Colonial Hotel

10/10 Excellent

"What's clean staff was friendly food was good bar was nice the buildings a little bit old "

[](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.Hotel-Information)

![The Inn At Crumpin Fox](https://images.trvl-media.com/lodging/5000000/4580000/4570100/4570044/b4ead30a_y.jpg)

### The Inn At Crumpin Fox

10/10 Excellent

"The room was very spacious and exceptionally clean. We enjoyed the sitting area by the large bay window. The gentleman at the counter was very friendly and helpful. He even shoveled the snow from my vehicle."

[](https://expedia.ca/Bernardston-Hotels-The-Inn-At-Crumpin-Fox.h4570044.Hotel-Information)

## Find out more about Winchester

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 Winchester. 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 Winchester ](https://expedia.ca/Winchester-Private-Vacation-Homes.d3000447144-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Winchester ](https://expedia.ca/Winchester-Cottages.d3000447144-aaCottages.Travel-Guide-Accommodation)
- [Apartments in Winchester ](https://expedia.ca/Winchester-Apartments.d3000447144-aaApartments.Travel-Guide-Accommodation)
- [Cabin Rentals in Winchester ](https://expedia.ca/Winchester-Cabins.d3000447144-aaCabins.Travel-Guide-Accommodation)
- [B&B in Winchester ](https://expedia.ca/Winchester-Bed-And-Breakfast.d3000447144-aaBedAndBreakfast.Travel-Guide-Accommodation)
- [Chalets in Winchester ](https://expedia.ca/Winchester-Chalets.d3000447144-aaChalets.Travel-Guide-Accommodation)
- [Guest Houses in Winchester ](https://expedia.ca/Winchester-Guest-Houses.d3000447144-aaGuestHouses.Travel-Guide-Accommodation)
- [Farmstay in Winchester ](https://expedia.ca/Winchester-Agritourism.d3000447144-aaAgritourism.Travel-Guide-Accommodation)
- [Motels in Winchester ](https://expedia.ca/Winchester-Motels.d3000447144-aaMotels.Travel-Guide-Accommodation)
- [Villas in Winchester ](https://expedia.ca/Winchester-Villas.d3000447144-aaVillas.Travel-Guide-Accommodation)
- [Lodges in Winchester ](https://expedia.ca/Winchester-Lodges.d3000447144-aaLodges.Travel-Guide-Accommodation)
- [RV Parks in Winchester ](https://expedia.ca/Winchester-RV-Parks.d3000447144-aaRVParks.Travel-Guide-Accommodation)
- [Inns in Winchester ](https://expedia.ca/Winchester-Inns.d3000447144-aaInns.Travel-Guide-Accommodation)
- [Condo Rentals in Winchester ](https://expedia.ca/Winchester-Condos.d3000447144-aaCondos.Travel-Guide-Accommodation)

## Frequently asked questions

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