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Winchester Vacation Rentals

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 mi
44 rentals in Winchester.
Beautiful lake side get away, quiet, and peaceful., vacation rental in Winchester
Beautiful lake side get away, quiet, and peaceful., vacation rental in Winchester
Beautiful lake side get away, quiet, and peaceful., vacation rental in Winchester

Beautiful lake side get away, quiet, and peaceful.

Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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You have found a clean and bright home on the water., vacation rental in Winchester
You have found a clean and bright home on the water., vacation rental in Winchester
You have found a clean and bright home on the water., vacation rental in Winchester

You have found a clean and bright home on the water.

Rental Home
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Story Book Lake Front Chateau with Private Beach!, vacation rental in Winchester
Story Book Lake Front Chateau with Private Beach!, vacation rental in Winchester
Story Book Lake Front Chateau with Private Beach!, vacation rental in Winchester

Story Book Lake Front Chateau with Private Beach!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Magical Lakefront Home in Forest Lake, vacation rental in Winchester
Magical Lakefront Home in Forest Lake, vacation rental in Winchester
Magical Lakefront Home in Forest Lake, vacation rental in Winchester

Magical Lakefront Home in Forest Lake

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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The following properties within 20 miles of Winchester match all your filters:
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!, vacation rental in Winchester
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!, vacation rental in Winchester
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!, vacation rental in Winchester

Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Spectacular Mountain views with all the amentities nearby, vacation rental in Winchester
Spectacular Mountain views with all the amentities nearby, vacation rental in Winchester
Spectacular Mountain views with all the amentities nearby, vacation rental in Winchester

Spectacular Mountain views with all the amentities nearby

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Unique second floor Private Studio with Coded Locks, vacation rental in Winchester
Unique second floor Private Studio with Coded Locks, vacation rental in Winchester
Unique second floor Private Studio with Coded Locks, vacation rental in Winchester

Unique second floor Private Studio with Coded Locks

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Fully Furnished 2bdrm/Pet Friendly!, vacation rental in Winchester
Fully Furnished 2bdrm/Pet Friendly!, vacation rental in Winchester
Fully Furnished 2bdrm/Pet Friendly!, vacation rental in Winchester

Fully Furnished 2bdrm/Pet Friendly!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Fully furnished/everything included/Pet Friendly!, vacation rental in Winchester
Fully furnished/everything included/Pet Friendly!, vacation rental in Winchester
Fully furnished/everything included/Pet Friendly!, vacation rental in Winchester

Fully furnished/everything included/Pet Friendly!

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna, vacation rental in Winchester
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna, vacation rental in Winchester
Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna, vacation rental in Winchester

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Downtown apartment ideal location to everything, vacation rental in Winchester
Downtown apartment ideal location to everything, vacation rental in Winchester
Downtown apartment ideal location to everything, vacation rental in Winchester

Downtown apartment ideal location to everything

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Artsy, Pet-Friendly Studio with a  Forest in the backyard, vacation rental in Winchester
Artsy, Pet-Friendly Studio with a  Forest in the backyard, vacation rental in Winchester
Artsy, Pet-Friendly Studio with a  Forest in the backyard, vacation rental in Winchester

Artsy, Pet-Friendly Studio with a Forest in the backyard

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Cabin on clean lake with great deck and dock, vacation rental in Winchester
Cabin on clean lake with great deck and dock, vacation rental in Winchester
Cabin on clean lake with great deck and dock, vacation rental in Winchester

Cabin on clean lake with great deck and dock

Rental Home
4 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Cozy Updated Log Cabin with Mountain Views close to Monadnock, vacation rental in Winchester
Cozy Updated Log Cabin with Mountain Views close to Monadnock, vacation rental in Winchester
Cozy Updated Log Cabin with Mountain Views close to Monadnock, vacation rental in Winchester

Cozy Updated Log Cabin with Mountain Views close to Monadnock

Rental Home
3 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Lake house getaway on pristine Spofford Lake, New Hampshire, vacation rental in Winchester
Lake house getaway on pristine Spofford Lake, New Hampshire, vacation rental in Winchester
Lake house getaway on pristine Spofford Lake, New Hampshire, vacation rental in Winchester

Lake house getaway on pristine Spofford Lake, New Hampshire

Rental Home
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Downtown Hot Tub Escape, vacation rental in Winchester
Downtown Hot Tub Escape, vacation rental in Winchester
Downtown Hot Tub Escape, vacation rental in Winchester

Downtown Hot Tub Escape

Rental Home
3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
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Picturesque Lakefront Retreat at Spofford Lake, vacation rental in Winchester
Picturesque Lakefront Retreat at Spofford Lake, vacation rental in Winchester
Picturesque Lakefront Retreat at Spofford Lake, vacation rental in Winchester

Picturesque Lakefront Retreat at Spofford Lake

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Penthouse, Steps to the Sandy Beach & clear water, vacation rental in Winchester
Penthouse, Steps to the Sandy Beach & clear water, vacation rental in Winchester
Penthouse, Steps to the Sandy Beach & clear water, vacation rental in Winchester

Penthouse, Steps to the Sandy Beach & clear water

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Waterfront House on Private Lake - Tranquil Location and Amazing Sunsets, vacation rental in Winchester
Waterfront House on Private Lake - Tranquil Location and Amazing Sunsets, vacation rental in Winchester
Waterfront House on Private Lake - Tranquil Location and Amazing Sunsets, vacation rental in Winchester

Waterfront House on Private Lake - Tranquil Location and Amazing Sunsets

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Main House, Relax and enjoy the scenery, go and swim, fish or start your boat, vacation rental in Winchester
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat, vacation rental in Winchester
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat, vacation rental in Winchester

Main House, Relax and enjoy the scenery, go and swim, fish or start your boat

Rental Home
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford, vacation rental in Winchester
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford, vacation rental in Winchester
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford, vacation rental in Winchester

Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford

Rental Home
4 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
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Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, vacation rental in Winchester
Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, vacation rental in Winchester
Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, vacation rental in Winchester

Victorian Lakefront Cottage With Spectacular Sunrise View Of Water

Rental Home
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
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Monadnock 4-Bedroom Charmer by Cheshire Rail Trail, vacation rental in Winchester
Monadnock 4-Bedroom Charmer by Cheshire Rail Trail, vacation rental in Winchester
Monadnock 4-Bedroom Charmer by Cheshire Rail Trail, vacation rental in Winchester

Monadnock 4-Bedroom Charmer by Cheshire Rail Trail

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake, vacation rental in Winchester
Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake, vacation rental in Winchester
Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake, vacation rental in Winchester

Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
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Historic Home w/ Modern Updates on < 4 Acres, vacation rental in Winchester
Historic Home w/ Modern Updates on < 4 Acres, vacation rental in Winchester
Historic Home w/ Modern Updates on < 4 Acres, vacation rental in Winchester

Historic Home w/ Modern Updates on < 4 Acres

Rental Home
7 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Hillside Haven: Luxe Farm Escape with 5BR - 2 King Bed - 2 Full Bath - Sleeps 10, vacation rental in Winchester
Hillside Haven: Luxe Farm Escape with 5BR - 2 King Bed - 2 Full Bath - Sleeps 10, vacation rental in Winchester
Hillside Haven: Luxe Farm Escape with 5BR - 2 King Bed - 2 Full Bath - Sleeps 10, vacation rental in Winchester

Hillside Haven: Luxe Farm Escape with 5BR - 2 King Bed - 2 Full Bath - Sleeps 10

Rental Home
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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200 y.o. Farmhouse secluded in its own valley with 2 ponds, vacation rental in Winchester
200 y.o. Farmhouse secluded in its own valley with 2 ponds, vacation rental in Winchester
200 y.o. Farmhouse secluded in its own valley with 2 ponds, vacation rental in Winchester

200 y.o. Farmhouse secluded in its own valley with 2 ponds

Rental Home
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Lake Front Scenic Home  6 bdrm with  3 &1/2 bath, vacation rental in Winchester
Lake Front Scenic Home  6 bdrm with  3 &1/2 bath, vacation rental in Winchester
Lake Front Scenic Home  6 bdrm with  3 &1/2 bath, vacation rental in Winchester

Lake Front Scenic Home 6 bdrm with 3 &1/2 bath

Rental Home
7 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Lake Front Bldg. Friendly Secluded/Wooded w. 6 Bedrms, vacation rental in Winchester
Lake Front Bldg. Friendly Secluded/Wooded w. 6 Bedrms, vacation rental in Winchester
Lake Front Bldg. Friendly Secluded/Wooded w. 6 Bedrms, vacation rental in Winchester

Lake Front Bldg. Friendly Secluded/Wooded w. 6 Bedrms

Rental Home
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Vikings Villages Resort - Double Bed Room, vacation rental in Winchester
Vikings Villages Resort - Double Bed Room, vacation rental in Winchester
Vikings Villages Resort - Double Bed Room, vacation rental in Winchester

Vikings Villages Resort - Double Bed Room

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Charming 2BR semi-rural home in Southern VT - amazing setting & modern amenities, vacation rental in Winchester
Charming 2BR semi-rural home in Southern VT - amazing setting & modern amenities, vacation rental in Winchester
Charming 2BR semi-rural home in Southern VT - amazing setting & modern amenities, vacation rental in Winchester

Charming 2BR semi-rural home in Southern VT - amazing setting & modern amenities

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Cozy, Rustic Summer Cabin on Clean Lake, vacation rental in Winchester
Cozy, Rustic Summer Cabin on Clean Lake, vacation rental in Winchester
Cozy, Rustic Summer Cabin on Clean Lake, vacation rental in Winchester

Cozy, Rustic Summer Cabin on Clean Lake

Rental Home
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Fully furnished 2 bdr apartment, vacation rental in Winchester
Fully furnished 2 bdr apartment, vacation rental in Winchester
Fully furnished 2 bdr apartment, vacation rental in Winchester

Fully furnished 2 bdr apartment

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 3
Match: Sleeps
More info
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Charming 3-bedroom farmhouse in fantastic Northfield with WiFi, AC, vacation rental in Winchester
Charming 3-bedroom farmhouse in fantastic Northfield with WiFi, AC, vacation rental in Winchester
Charming 3-bedroom farmhouse in fantastic Northfield with WiFi, AC, vacation rental in Winchester

Charming 3-bedroom farmhouse in fantastic Northfield with WiFi, AC

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Studio w/ Trail Access ~ 10 Mi to Brattleboro!, vacation rental in Winchester
Studio w/ Trail Access ~ 10 Mi to Brattleboro!, vacation rental in Winchester
Studio w/ Trail Access ~ 10 Mi to Brattleboro!, vacation rental in Winchester

Studio w/ Trail Access ~ 10 Mi to Brattleboro!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Cozy Home Near Downtown, Shops, and Restaurants., vacation rental in Winchester
Cozy Home Near Downtown, Shops, and Restaurants., vacation rental in Winchester
Cozy Home Near Downtown, Shops, and Restaurants., vacation rental in Winchester

Cozy Home Near Downtown, Shops, and Restaurants.

Rental Home
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!, vacation rental in Winchester
Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!, vacation rental in Winchester
Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!, vacation rental in Winchester

Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
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Sauna and Mountain Views, the Perfect Cozy Vermont Getaway, vacation rental in Winchester
Sauna and Mountain Views, the Perfect Cozy Vermont Getaway, vacation rental in Winchester
Sauna and Mountain Views, the Perfect Cozy Vermont Getaway, vacation rental in Winchester

Sauna and Mountain Views, the Perfect Cozy Vermont Getaway

Rental Home
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
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Cozy home in Brattleboro, vacation rental in Winchester
Cozy home in Brattleboro, vacation rental in Winchester
Cozy home in Brattleboro, vacation rental in Winchester

Cozy home in Brattleboro

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Cozy 1-bedroom apartment in delightful Brattleboro, vacation rental in Winchester
Cozy 1-bedroom apartment in delightful Brattleboro, vacation rental in Winchester
Cozy 1-bedroom apartment in delightful Brattleboro, vacation rental in Winchester

Cozy 1-bedroom apartment in delightful Brattleboro

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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The Covey House Retreat with InfraRed Sauna, vacation rental in Winchester
The Covey House Retreat with InfraRed Sauna, vacation rental in Winchester
The Covey House Retreat with InfraRed Sauna, vacation rental in Winchester

The Covey House Retreat with InfraRed Sauna

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options, vacation rental in Winchester
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options, vacation rental in Winchester
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options, vacation rental in Winchester

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

Rental Home
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Fully furnished/Pet Friendly!, vacation rental in Winchester
Fully furnished/Pet Friendly!, vacation rental in Winchester
Fully furnished/Pet Friendly!, vacation rental in Winchester

Fully furnished/Pet Friendly!

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Peaceful lake front home on beautiful Spofford Lake!, vacation rental in Winchester
Peaceful lake front home on beautiful Spofford Lake!, vacation rental in Winchester
Peaceful lake front home on beautiful Spofford Lake!, vacation rental in Winchester

Peaceful lake front home on beautiful Spofford Lake!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Showing results 1-44 of 44
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