Title: Winchester Vacation Rentals from CA $218: 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

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two 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)

In three months

[Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=3000447144&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)

In four months

[Jul 24 - Jul 26](https://www.expedia.ca/Hotel-Search?regionId=3000447144&startDate=2026-07-24&endDate=2026-07-26&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

![Outdoor dining](https://images.trvl-media.com/lodging/124000000/123130000/123128400/123128344/e4e41d9e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/124000000/123130000/123128400/123128344/6c48878a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/124000000/123130000/123128400/123128344/55d30d8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/124000000/123130000/123128400/123128344/58d928d0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 2 private mountain RV pads for rent. Full hook ups

[](https://www.expedia.ca/Winchester-Hotels-2-Private-Mountain-RV-Pads-For-Rent-Full-Hook-Ups.h123128344.Hotel-Information)

Winchester

CA $61

CA $97 total

includes taxes & fees

May 1 - May 2

[](https://www.expedia.ca/Winchester-Hotels-2-Private-Mountain-RV-Pads-For-Rent-Full-Hook-Ups.h123128344.Hotel-Information)

![Terrace/patio](https://images.trvl-media.com/lodging/111000000/110600000/110594900/110594861/29a39361.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fireplace](https://images.trvl-media.com/lodging/111000000/110600000/110594900/110594861/0c027b4c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Miscellaneous](https://images.trvl-media.com/lodging/111000000/110600000/110594900/110594861/e60f9f5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/111000000/110600000/110594900/110594861/90945353.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options

[](https://www.expedia.ca/Hinsdale-Hotels-RESTful-Yurt-In-Charming-Hinsdale-Pet-Friendly-With-Multiple-Hiking-Options.h110594861.Hotel-Information)

Hinsdale

10/10

Exceptional

(11 reviews)

"Yert was perfect and stocked with everything we needed,property owner showed up to make sure we had everything we needed then left us in complete privacy,location was amazing with a great scenic view."

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

Jerry S.

CA $125

CA $218 total

includes taxes & fees

Apr 11 - Apr 12

[](https://www.expedia.ca/Hinsdale-Hotels-RESTful-Yurt-In-Charming-Hinsdale-Pet-Friendly-With-Multiple-Hiking-Options.h110594861.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)

![2 bedrooms, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/6c4ecd64.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)

![Smart TV, fireplace, books](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/e7a2f4c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin & Sauna on Lake Monomonac near Mt. Monadnock

[](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 $288

CA $458 total

includes taxes & fees

Apr 5 - Apr 6

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

![Interior](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/e9dcc51b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106480000/106477000/106476934/6faf555f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cabin & Sauna on Lake Monomonac near Mt. Monadnock

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

Rindge

10/10

Exceptional

(12 reviews)

"Super cute cabin. It was winter so we didn’t get to see a lot of the lake/property but everything was very comfortable and Jim was a fantastic host. Would definitely stay again! "

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

Rebecca

CA $229

CA $367 total

includes taxes & fees

Apr 8 - Apr 9

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

![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)

![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)

![Dining](https://images.trvl-media.com/lodging/103000000/102240000/102238400/102238328/8c094e30.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

(33 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 $119

CA $235 total

includes taxes & fees

Apr 14 - Apr 15

[](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/103000000/102390000/102386600/102386531/512b2604.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

(52 reviews)

"Very clean, cozy and lots of nice plants! "

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

Mary

CA $162

CA $282 total

includes taxes & fees

Apr 5 - Apr 6

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

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

![Interior](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/fc0d0a2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/w956h736x34y34-3e10a6af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106420000/106418500/106418444/0a827c6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Wellness Getaway with a Personal Sauna, and Private River Beach!

[](https://www.expedia.ca/Newfane-Hotels-Wellness-Getaway-With-A-Personal-Sauna.h106418444.Hotel-Information)

Newfane

10/10

Exceptional

(3 reviews)

"Very welcoming and extremely helpful. Had a wonderful stay post ski day! Would definitely recommend and stay again. "

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

Joseph P.

CA $188

CA $355 total

includes taxes & fees

Apr 14 - Apr 15

[](https://www.expedia.ca/Newfane-Hotels-Wellness-Getaway-With-A-Personal-Sauna.h106418444.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)

![Interior](https://images.trvl-media.com/lodging/111000000/110900000/110890700/110890615/d3aa8c7e.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 $383

CA $474 total

includes taxes & fees

Apr 5 - Apr 6

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

![Exterior](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/5dd08019.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/14aa4f5f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/94d9ae76.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)

### Cabin & Sauna on Lake Monomonac near Mt. Monadnock

[](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 $263

CA $443 total

includes taxes & fees

Apr 19 - Apr 20

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

![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)

![Property grounds](https://images.trvl-media.com/lodging/124000000/123530000/123526000/123525991/fda99bfd.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.

CA $184

CA $377 total

includes taxes & fees

Apr 6 - Apr 7

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

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124180000/124177600/124177563/c93e763c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124180000/124177600/124177563/f8f558ba.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124180000/124177600/124177563/95da5fd9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House (4 Bedrooms) | Interior](https://images.trvl-media.com/lodging/125000000/124180000/124177600/124177563/fad6cb80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Outdoor Adventure Hub! Family Home in West Dover

[](https://www.expedia.ca/West-Dover-Hotels-Ski.h124177563.Hotel-Information)

West Dover

CA $213

CA $726 total

includes taxes & fees

Apr 4 - Apr 5

[](https://www.expedia.ca/West-Dover-Hotels-Ski.h124177563.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/121000000/120540000/120530700/120530639/4d1d83e0.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)

![Living area](https://images.trvl-media.com/lodging/121000000/120540000/120530700/120530639/6d6cf781.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Hair dryer, towels, soap, toilet paper](https://images.trvl-media.com/lodging/121000000/120540000/120530700/120530639/8db5164c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming Country-Chic 1BR in Greenfield – King Bed, Rain Shower, Near Berkshires

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

Greenfield

9.6/10

Exceptional

(8 reviews)

"Super clean and nice space with beautifully updated bathroom and kitchen. Loved staying here."

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

Andrew R.

CA $127

CA $336 total

includes taxes & fees

Apr 8 - Apr 9

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

![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)

![Interior](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/89c4c4df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor spa tub](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/d85bd4e5.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-Modern-Downtown-12ppl-Hot-Tub-Fire-Pit-Games.h97317603.Hotel-Information)

Keene

9.6/10

Exceptional

(22 reviews)

"Nice house in a nice location. "

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

Rob B.

CA $201

CA $421 total

includes taxes & fees

Apr 6 - Apr 7

[](https://www.expedia.ca/Keene-Hotels-Modern-Downtown-12ppl-Hot-Tub-Fire-Pit-Games.h97317603.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)

![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)

![3 bedrooms, WiFi](https://images.trvl-media.com/lodging/69000000/68720000/68712000/68711922/4c6a2082.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)

### 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 $287

CA $355 total

includes taxes & fees

Apr 6 - Apr 7

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

![Exterior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039338/5bbd846e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Living area](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039338/e86ed09e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, desk, iron/ironing board, WiFi](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039338/6d462fcf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/121000000/120040000/120039400/120039338/23c80aaf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Rose wisteria 4 guests 2 bedrooms-full+queen beds

[](https://www.expedia.ca/Shelburne-Falls-Hotels-Rose-Wisteria-4-Guests-2-Bedrooms-Fullqueen-Beds.h120039338.Hotel-Information)

Shelburne Falls

CA $216

CA $416 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Shelburne-Falls-Hotels-Rose-Wisteria-4-Guests-2-Bedrooms-Fullqueen-Beds.h120039338.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/128000000/127210000/127200300/127200284/c273eae2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/128000000/127210000/127200300/127200284/b8fc4795.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/128000000/127210000/127200300/127200284/259a2154.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/128000000/127210000/127200300/127200284/423b25a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Light-filled treetop apartment close to downtown Greenfield and Highland Park

[](https://www.expedia.ca/Greenfield-Hotels-Light-Filled-Treetop-Apartment-Close-To-Downtown-Greenfield-And-Highland-Park.h127200284.Hotel-Information)

Greenfield

10/10

Exceptional

(1 review)

"Pros: The apartment is beautiful. Lots of natural lights, sky windows, clean, bathtub has a jacuzzi, clean linens and very positive environment. Host is quick on responding and is super sweet. Privacy and lots of nature. You can literally be indoors and enjoy nature. Cons: not for people with bad knees as lots of stairs to reach to the apartment. For reference: I did not need it but there were no condiments except salt, no knife, no scissors, no laundry (this is mentioned in listing). "

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

Neha Maheshkumar

CA $154

CA $203 total

includes taxes & fees

Apr 15 - Apr 16

[](https://www.expedia.ca/Greenfield-Hotels-Light-Filled-Treetop-Apartment-Close-To-Downtown-Greenfield-And-Highland-Park.h127200284.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)

![Terrace/patio](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/ad9f4a52.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)

![Smart TV, fireplace, printers](https://images.trvl-media.com/lodging/89000000/88310000/88302100/88302089/c66c8a42.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 $232

CA $501 total

includes taxes & fees

Apr 16 - Apr 17

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/c077bee3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/1ae2e1b6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Game room](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/eb8c4f2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/b4b598c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spacious 5BR w/ Hot Tub & Games

[](https://www.expedia.ca/Colrain-Hotels-10-Guests-5-BR.h37817199.Hotel-Information)

Colrain

9.8/10

Exceptional

(48 reviews)

"Great house for family gatherings "

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

John Paul B.

CA $394

CA $904 total

includes taxes & fees

Apr 5 - Apr 6

[](https://www.expedia.ca/Colrain-Hotels-10-Guests-5-BR.h37817199.Hotel-Information)

![Property grounds](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/a4ec6964.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w2207h1242x0y0-824667c2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/73e1d55a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Books](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w960h638x0y1-6a5c7328.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

###  Family Friendly Hilltop House In Putney Vermont

[](https://www.expedia.ca/Putney-Hotels-Pet-And-Family-Friendly-Hilltop-House-In-Putney-Vermont.h19887179.Hotel-Information)

Putney

9.4/10

Exceptional

(59 reviews)

"The host and her daughter were lovely and kind and very quick with all communication."

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

Susan O.

CA $219

CA $412 total

includes taxes & fees

Apr 17 - Apr 18

[](https://www.expedia.ca/Putney-Hotels-Pet-And-Family-Friendly-Hilltop-House-In-Putney-Vermont.h19887179.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)

![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/114000000/113160000/113155300/113155266/41130fc2.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)

### 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 $118

CA $285 total

includes taxes & fees

Apr 9 - Apr 10

[](https://www.expedia.ca/East-Dover-Hotels-Cozy-Apt-In-Beautiful-Secluded-Spot-15-Mins-From-Mt-Snow.h113155266.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=2026-04-17&endDate=2026-04-18&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=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=CABIN)

Cottages

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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=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=APARTMENT)

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=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=VACATION_HOME)

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=2026-07-02&d1=2026-07-02&endDate=2026-07-05&d2=2026-07-05&lodging=CHALET)

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## Top Winchester Hotel Reviews

![Holiday Inn Express Hotel & Suites Brattleboro by IHG](https://images.trvl-media.com/lodging/1000000/850000/845500/845427/50bc8764_y.jpg)

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

10/10 Excellent

"Very pleasant stay! Room was clean staff friendly and breakfast hearty. "

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

![Travelodge by Wyndham Brattleboro VT](https://images.trvl-media.com/lodging/2000000/1040000/1039700/1039680/19b6c01d_y.jpg)

### Travelodge by Wyndham Brattleboro VT

8/10 Good

"It was fairly clean room was cold however the staff was amazing, Awesome Customer Service skills and flexibility to accommodate my needs. I will definitely recommend to others. "

[](https://expedia.ca/Brattleboro-Hotels-Travelodge-By-Wyndham-Brattleboro-VT.h1039680.Hotel-Information)

![Best Western Plus Keene Hotel](https://images.trvl-media.com/lodging/1000000/20000/16000/15916/w3837h2556x3y4-4a5edcca_y.jpg)

### Best Western Plus Keene Hotel

10/10 Excellent

"One of the better franchise hotels I've stayed at for this price point."

[](https://expedia.ca/Keene-Hotels-Best-Western-Plus-Keene-Hotel.h15916.Hotel-Information)

![The Putney Inn](https://images.trvl-media.com/lodging/2000000/1820000/1810900/1810866/acae342c_y.jpg)

### The Putney Inn

10/10 Excellent

"I stayed just for a night and it was the best hotel sleep I’ve had in ages. Check in was easy, staff were lovely, and parking was plentiful. "

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

![Colonial Motel And Spa](https://images.trvl-media.com/lodging/2000000/1080000/1070800/1070729/05f7e3bc_y.jpg)

### Colonial Motel And Spa

4/10 Poor

"Plenty of parking Clean - no bugs Goes downhill from there. Front desk people were polite but far from friendly. Major renovations need to be done before I will come back. Windows did not lock, which my husband discovered as we were getting ready for bed. He decided that they were too small for anyone to crawl through, but not a comforting feeling. Pool - closes at 5pm on Sunday - we arrived at 5:10 😳 Hot tub - closed for cleaning on Monday until 1pm, but check out is at 11am So I have no idea what the condition is of either, but I cannot imagine that they are in great shape. I should have known that 2 pools and a hot tub for that price was too good to be true "

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

![Latchis Hotel](https://images.trvl-media.com/lodging/2000000/1370000/1367300/1367207/4c998aa8_y.jpg)

### Latchis Hotel

10/10 Excellent

"If you love retro/vintage/history/ quiet and pet friendly this place is wonderful for a short stay and lowkey weekend. So many cool local businesses and delicious food. We went for a show at the stone church- walking distance from hotel! And everything we could have needed was easily accessible. They have a bar downstairs and a movie theatre in the hotel! All rooms have record players and vinyls to play with more available. Big rooms. “Dated” but it’s keeping with the retro style- very clean and neat. Only negatives were the parking lot (really small but we got a spot! There’s plenty of on street parking and a nearby parking garage as well). Staff was so friendly and helpful! This would be a great “staycation” or mom night away as well. Stop at some of the amazing thrift/vintage/2nd hand stores for books, music, clothes and more. If you’re a crafter, Bobbins’and Skeins and Beadnik are great places to take a look at. I’d definitely come back!"

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

![Hampton Inn Brattleboro](https://images.trvl-media.com/lodging/2000000/1160000/1158100/1158047/44065a1d_y.jpg)

### Hampton Inn Brattleboro

10/10 Excellent

"Nice"

[](https://expedia.ca/Brattleboro-Hotels-Hampton-Inn-Brattleboro.h1158047.Hotel-Information)

![The Covered Bridge Inn](https://images.trvl-media.com/lodging/28000000/27670000/27661400/27661353/10a69b41_y.jpg)

### The Covered Bridge Inn

4/10 Poor

"The rrooms were clean, shower was great. Hallways dark, parking lot not to much lighting. There is no breakfast just coffee."

[](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/ad889baf_y.jpg)

### The Colonial Hotel

10/10 Excellent

"Comfortable bed, everything was neat and tidy."

[](https://expedia.ca/Leominster-Hotels-The-Colonial-Hotel.h40458.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)
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## Frequently asked questions

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