Title: Winchester Vacation Rentals from $154: Search Short-Term Rentals | Expedia.com

[Winchester Travel Guide](https://expedia.com/Winchester.dx3000447144)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d3000447144.Travel-Guide-Hotels)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d3000447144.Travel-Guide-Flights)[Car Rentals in Winchester](https://expedia.com/Car-Rentals-In-Winchester.d3000447144.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.com/Winchester.d3000447144.Destination-Travel-Guides)

![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

[Mar 20 - Mar 22](https://www.expedia.com/Hotel-Search?regionId=3000447144&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[May 1 - May 3](https://www.expedia.com/Hotel-Search?regionId=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 three months

[May 29 - May 31](https://www.expedia.com/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 four months

[Jun 26 - Jun 28](https://www.expedia.com/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)

## Our top choices for Winchester vacation rentals

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

![Interior](https://images.trvl-media.com/lodging/109000000/108330000/108320100/108320042/b4e38c32.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)

### Lake Whitingham & Mount Snow Area Village Apartment

[](https://www.expedia.com/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.

$274 nightly

$307 total

Mar 7 - Mar 8

Total with taxes and fees

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

![Exterior detail](https://images.trvl-media.com/lodging/103000000/102390000/102386600/102386531/d695e72e.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)

![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)

### Lovely 2nd Floor Apartment

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

Greenfield

10/10

Exceptional

(49 reviews)

"This is a comfortable and spacious apartment in a great location central to everything in Greenfield. David is also an excellent host who communicated clearly throughout our visit. Would definitely stay here again. "

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

Geoffrey B.

$180 nightly

$201 total

Mar 10 - Mar 11

Total with taxes and fees

[](https://www.expedia.com/Greenfield-Hotels-Lovely-2nd-Floor-Apartment.h102386531.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/111000000/110900000/110890700/110890615/07d1d9b9.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)

### Vikings Villages Resort - Double Bed Room

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

Guilford

$275 nightly

$279 total

Mar 8 - Mar 9

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/84000000/83070000/83064100/83064044/bb59d3ab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83070000/83064100/83064044/0e213458.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![3 bedrooms, free WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83070000/83064100/83064044/ee57533b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Dining](https://images.trvl-media.com/lodging/84000000/83070000/83064100/83064044/870b92e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Enjoy your stay in an antique home in an antique toy museum!

[](https://www.expedia.com/Winchendon-Hotels-Enjoy-Your-Stay-In-An-Antique-Home-In-An-Antique-Toy-Museum.h83064044.Hotel-Information)

Winchendon

9.4/10

Exceptional

(8 reviews)

"What a fun stay! Great communication with the property manager Don, cute town, lots of American history to be discovered, fun stay. 10/10 highly recommend!!!"

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

Katja Z.

$491 nightly

$519 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Winchendon-Hotels-Enjoy-Your-Stay-In-An-Antique-Home-In-An-Antique-Toy-Museum.h83064044.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)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106340000/106335700/106335693/d2180d1c.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)

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

[](https://www.expedia.com/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.

$304 nightly

$330 total

Mar 8 - Mar 9

Total with taxes and fees

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

![Smart TV, books](https://images.trvl-media.com/lodging/38000000/37820000/37817200/37817199/212e023d.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)

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

### Colrain Spring into Adventure HotTub AirHockey Firepit

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

Colrain

9.8/10

Exceptional

(47 reviews)

"Great house for family gatherings "

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

John Paul B.

$573 nightly

$640 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Colrain-Hotels-10-Guests-5-BR.h37817199.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/de082b20.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)

![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)

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

[](https://www.expedia.com/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.

$223 nightly

$250 total

Mar 18 - Mar 19

Total with taxes and fees

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

![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)

![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)

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

[](https://www.expedia.com/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.

$244 nightly

$265 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Walpole-Hotels-Cozy-Farm-Cottage-On-Gorgeous-Landscape.h68711922.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.com/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.

$229 nightly

$256 total

Mar 20 - Mar 21

Total with taxes and fees

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

![Terrace/patio](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/1a650c93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/e3b7abc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books, video library](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/18ad0df8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33970000/33961400/33961365/4c5c4ab9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Lg/Charming Updated Farmhouse Historic Picturesque Walpole NH/VT Border sleeps 9

[](https://www.expedia.com/Keene-Hotels-Charming-Updated-Farmhouse-In-Historic-Picturesque-Walpole-NH-And-Sleeps-8.h33961365.Hotel-Information)

Walpole

10/10

Exceptional

(50 reviews)

"We had a very lovely stay. "

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

mary c.

$545 nightly

$591 total

Mar 9 - Mar 10

Total with taxes and fees

[](https://www.expedia.com/Keene-Hotels-Charming-Updated-Farmhouse-In-Historic-Picturesque-Walpole-NH-And-Sleeps-8.h33961365.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)

![Property grounds](https://images.trvl-media.com/lodging/107000000/106490000/106490000/106489950/53ea3769.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)

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

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

[](https://www.expedia.com/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

$253 nightly

$275 total

Mar 8 - Mar 9

Total with taxes and fees

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

![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)

![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.com/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.

$314 nightly

$341 total

Mar 8 - Mar 9

Total with taxes and fees

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

![Interior](https://images.trvl-media.com/lodging/98000000/97320000/97317700/97317603/89c4c4df.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.com/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.

$262 nightly

$284 total

Apr 5 - Apr 6

Total with taxes and fees

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

![Exterior](https://images.trvl-media.com/lodging/126000000/125300000/125300000/125299924/f2b21706.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)

![Private kitchen](https://images.trvl-media.com/lodging/126000000/125300000/125300000/125299924/94e00bfc.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)

### Cozy & Bright Guest Suite

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

Peterborough

$193 nightly

$210 total

Mar 8 - Mar 9

Total with taxes and fees

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

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

![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110600000/110594900/110594861/8467145b.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)

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

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

Hinsdale

10/10

Exceptional

(10 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.

$150 nightly

$162 total

Mar 19 - Mar 20

Total with taxes and fees

[](https://www.expedia.com/Hinsdale-Hotels-RESTful-Yurt-In-Charming-Hinsdale-Pet-Friendly-With-Multiple-Hiking-Options.h110594861.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/107000000/106480000/106477000/106476934/6faf555f.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)

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

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

Rindge

10/10

Exceptional

(12 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.

$241 nightly

$262 total

Mar 8 - Mar 9

Total with taxes and fees

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74160000/74153700/74153605/a9fb4c80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74160000/74153700/74153605/23ddfec7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![5 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/75000000/74160000/74153700/74153605/c4e70041.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/75000000/74160000/74153700/74153605/65c29758.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cobb Meadow House - Cozy 5 Bedroom New England home in The Monadnock Region

[](https://www.expedia.com/Dublin-Hotels-5-Bedroom-Cozy-New-England-Home-Cobb-Meadow-House.h74153605.Hotel-Information)

Dublin

10/10

Exceptional

(26 reviews)

"Good place to stay during a wedding week"

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

Veronique S.

$541 nightly

$572 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Dublin-Hotels-5-Bedroom-Cozy-New-England-Home-Cobb-Meadow-House.h74153605.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)

![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)

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

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

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

Shelburne Falls

$264 nightly

$295 total

Mar 9 - Mar 10

Total with taxes and fees

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

![Books](https://images.trvl-media.com/lodging/20000000/19890000/19887200/19887179/w1125h1933x0y49-6292efb5.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)

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

###  Family Friendly Hilltop House In Putney Vermont

[](https://www.expedia.com/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.

$243 nightly

$272 total

Apr 6 - Apr 7

Total with taxes and fees

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

![Living area](https://images.trvl-media.com/lodging/125000000/124520000/124515900/124515804/878470a2.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/125000000/124520000/124515900/124515804/38754554.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/125000000/124520000/124515900/124515804/21da4a2c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Private kitchen](https://images.trvl-media.com/lodging/125000000/124520000/124515900/124515804/dcb4e261.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

[](https://www.expedia.com/Jacksonville-Hotels-Free-HOT-Breakfast-For-Each-Guest-Everyday-Located-In-Charming-Whitingham.h124515804.Hotel-Information)

Whitingham

$535 nightly

$599 total

Mar 8 - Mar 9

Total with taxes and fees

[](https://www.expedia.com/Jacksonville-Hotels-Free-HOT-Breakfast-For-Each-Guest-Everyday-Located-In-Charming-Whitingham.h124515804.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

[View all properties](https://expedia.com/Hotel-Search?startDate=2026-03-20&endDate=2026-03-21&regionId=3000447144&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

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## 

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[Book now](https://expedia.com/deals?rfrr=VR_SPRING_PROMO_3000447144)

## Find vacation rentals that suit your style

Cabins

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America&regionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&lodging=CABIN)

Cottages

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America&regionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&lodging=COTTAGE)

Private vacation homes

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America&regionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&lodging=VACATION_HOME)

Apartments

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America&regionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&lodging=APARTMENT)

Chalets

[](https://www.expedia.com/Hotel-Search?destination=Winchester%2C+New+Hampshire%2C+United+States+of+America&regionId=3000447144&latLong=42.773418%2C-72.383141&adults=2&startDate=2026-06-04&d1=2026-06-04&endDate=2026-06-07&d2=2026-06-07&lodging=CHALET)

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## Top Winchester Hotel Reviews

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

### The Putney Inn

10/10 Excellent

"clean room. Quiet place."

[](https://expedia.com/Putney-Hotels-The-Putney-Inn.h1810866.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

"I liked it a lot for the one night stop "

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

![Vikings Villages Resort](https://images.trvl-media.com/lodging/93000000/92080000/92078600/92078509/1221c604_y.jpg)

### Vikings Villages Resort

10/10 Excellent

"This place was amazing! The gentleman that checked me in was friendly and professional, he answered all my curiosity questions about the property. The room was so cool... lots of details put into the decor, comfortable bed, great shower pressure, full kitchen, quiet, nice wooded view from the bedroom window. I would absolutely stay here again."

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

![Courtyard by Marriott Keene Downtown](https://images.trvl-media.com/lodging/4000000/3560000/3555900/3555821/9384b42d_y.jpg)

### Courtyard by Marriott Keene Downtown

10/10 Excellent

"Great"

[](https://expedia.com/Keene-Hotels-Courtyard-By-Marriott-Keene-Downtown.h3555821.Hotel-Information)

![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

"Breakfast was great and the pool was nice"

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

![Hampton Inn & Suites Greenfield](https://images.trvl-media.com/lodging/2000000/1610000/1601100/1601018/1b1adba5_y.jpg)

### Hampton Inn & Suites Greenfield

8/10 Good

"Room was clean though the shampoo and body soap containers in the shower were empty. Too late to step out & look for both! Staff very welcoming and friendly."

[](https://expedia.com/Greenfield-Hotels-Hampton-Inn-Suites-Greenfield.h1601018.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

"There are two sections to the property. We asked to switch rooms because it smelled moldy on the one side. The other was in much better conditions, no smell, rooms very large, and clean. The pool is run by another company and they are strict about pool hours. "

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

![The Colonial Hotel](https://images.trvl-media.com/lodging/1000000/50000/40500/40458/93940b92_y.jpg)

### The Colonial Hotel

4/10 Poor

"This property needs a serious update. The property looks tired. Attempted to use the fitness room and it was dirty and much of the equipment was unusable. The pool and jacuzzi were closed and looked disgusting. The common areas and room felt unclean "

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

![Keene Elm City Hotel, an Ascend Collection Hotel](https://images.trvl-media.com/lodging/1000000/20000/14500/14439/dd472136_y.jpg)

### Keene Elm City Hotel, an Ascend Collection Hotel

6/10 Okay

"Staff was good, room needs updating "

[](https://expedia.com/Keene-Hotels-Holiday-Inn-Express-Keene.h14439.Hotel-Information)

## Find out more about Winchester

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

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

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

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

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

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $154 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

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

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

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

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

## Explore a world of travel with Expedia

- Trending destinations on Expedia.com
- All accommodation types in Winchester

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- [Pigeon Forge Vacation Rentals ](https://www.expedia.com/Pigeon-Forge-Vacation-Rentals.d8264.Travel-Guide-VacationRentals)
- [Ocean City Vacation Rentals ](https://www.expedia.com/Ocean-City-Vacation-Rentals.d9151.Travel-Guide-VacationRentals)
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- [Siesta Key Vacation Rentals ](https://www.expedia.com/Siesta-Key-Vacation-Rentals.d6881.Travel-Guide-VacationRentals)
- [Galveston Vacation Rentals ](https://www.expedia.com/Galveston-Vacation-Rentals.d1341.Travel-Guide-VacationRentals)
- [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals)
- [Palm Springs Vacation Rentals ](https://www.expedia.com/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals)
- [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals)
- [Lake Tahoe Vacation Rentals ](https://www.expedia.com/South-Lake-Tahoe-Vacation-Rentals.d10150.Travel-Guide-VacationRentals)
- [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals)
- [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations)
- [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations)
- [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations)

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

## Frequently asked questions

### Can I find a vacation rental in Winchester?

### What's the top vacation rental that Winchester has to offer?

### What’s there to see and do in Winchester?

### What’s a vacation rental in Winchester like?

### Expedia's Latest Trends

Hotels

- [Plymouth Hotels](https://expedia.com/Plymouth-Hotels.d6057411.Travel-Guide-Hotels)
- [Gorham Hotels](https://expedia.com/Gorham-Hotels.d10627.Travel-Guide-Hotels)
- [Manchester Cheap Hotels](https://expedia.com/Manchester-Hotels-Cheap-Hotels.0-0-d6025582-tCheapHotels.Travel-Guide-Filter-Hotels)
- [Hampton Hotels](https://expedia.com/Hampton-Hotels.d8268.Travel-Guide-Hotels)
- [Dover Hotels](https://expedia.com/Dover-Hotels.d7897.Travel-Guide-Hotels)
- [Hanover Hotels](https://expedia.com/Hanover-Hotels.d6069.Travel-Guide-Hotels)
- [Lebanon Hotels](https://expedia.com/Lebanon-Hotels.d2041.Travel-Guide-Hotels)
- [Hampton Oceanfront Hotels](https://expedia.com/Hampton-Hotels-Oceanfront-Hotels.0-0-d8268-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
- [Littleton Hotels](https://expedia.com/Littleton-Hotels.d55799.Travel-Guide-Hotels)
- [Keene Hotels](https://expedia.com/Keene-Hotels.d6057413.Travel-Guide-Hotels)
- [Laconia Hotels](https://expedia.com/Laconia-Hotels.d6057409.Travel-Guide-Hotels)
- [Lincoln Hotels](https://expedia.com/Lincoln-Hotels.d126059.Travel-Guide-Hotels)
- [Manchester Hotels](https://expedia.com/Manchester-Hotels.d6025582.Travel-Guide-Hotels)
- [Concord Hotels](https://expedia.com/Concord-Hotels.d6656.Travel-Guide-Hotels)
- [Portsmouth Hotels](https://expedia.com/Portsmouth-Hotels.d6057414.Travel-Guide-Hotels)
- [Meredith Hotels](https://expedia.com/Meredith-Hotels.d132500.Travel-Guide-Hotels)
- [Derry Hotels](https://expedia.com/Derry-Hotels.d3000446887.Travel-Guide-Hotels)
- [North Woodstock Hotels](https://expedia.com/North-Woodstock-Hotels.d183577.Travel-Guide-Hotels)
- [North Conway Hotels](https://expedia.com/North-Conway-Hotels.d9624.Travel-Guide-Hotels)
- [Salem Hotels](https://expedia.com/Salem-Hotels.d6603.Travel-Guide-Hotels)
- [Nashua Hotels](https://expedia.com/Nashua-Hotels.d6167.Travel-Guide-Hotels)
- [Gilford Hotels](https://expedia.com/Gilford-Hotels.d55723.Travel-Guide-Hotels)

Flights

- [Flights from Portsmouth](https://expedia.com/lp/flights/6057414/flights-from-portsmouth)
- [Flights to Manchester](https://expedia.com/Cheap-Flights-To-Manchester.d6025582.Travel-Guide-Flights)
- [Flights to Portsmouth](https://expedia.com/Cheap-Flights-To-Portsmouth.d6057414.Travel-Guide-Flights)

Cars

- [Car rentals in Portsmouth](https://expedia.com/Car-Rentals-In-Portsmouth.d6057414.Car-Rental-Guide)
- [Car rentals in Manchester](https://expedia.com/Car-Rentals-In-Manchester.d6025582.Car-Rental-Guide)

General

- [Visit North Conway](https://expedia.com/North-Conway.dx9624)
- [Visit North Woodstock](https://expedia.com/North-Woodstock.dx183577)
- [Visit Manchester](https://expedia.com/Manchester.dx6025582)

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