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Winchester Holiday Apartments

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Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

5 km
44 rentals in Winchester.
Beautiful lake side get away, quiet, and peaceful., holiday rental in Winchester
Beautiful lake side get away, quiet, and peaceful., holiday rental in Winchester
Beautiful lake side get away, quiet, and peaceful., holiday 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., holiday rental in Winchester
You have found a clean and bright home on the water., holiday rental in Winchester
You have found a clean and bright home on the water., holiday rental in Winchester

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

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

Story Book Lake Front Chateau with Private Beach!

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

Magical Lakefront Home in Forest Lake

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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The following properties within 32 kms of Winchester match all your filters:
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!, holiday rental in Winchester
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!, holiday rental in Winchester
Cozy 'Fiddler's Rest:' Cabin: 11 Miles to Skiing!, holiday rental in Winchester

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

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

Spectacular Mountain views with all the amentities nearby

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

Unique second floor Private Studio with Coded Locks

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
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Fully Furnished 2bdrm/Pet Friendly!, holiday rental in Winchester
Fully Furnished 2bdrm/Pet Friendly!, holiday rental in Winchester
Fully Furnished 2bdrm/Pet Friendly!, holiday 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!, holiday rental in Winchester
Fully furnished/everything included/Pet Friendly!, holiday rental in Winchester
Fully furnished/everything included/Pet Friendly!, holiday rental in Winchester

Fully furnished/everything included/Pet Friendly!

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

Tranquil Guest House - Peaceful Sanctuary plus InfraRed Sauna

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Downtown apartment ideal location to everything, holiday rental in Winchester
Downtown apartment ideal location to everything, holiday rental in Winchester
Downtown apartment ideal location to everything, holiday rental in Winchester

Downtown apartment ideal location to everything

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Artsy, Pet-Friendly Studio with a  Forest in the backyard, holiday rental in Winchester
Artsy, Pet-Friendly Studio with a  Forest in the backyard, holiday rental in Winchester
Artsy, Pet-Friendly Studio with a  Forest in the backyard, holiday 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, holiday rental in Winchester
Cabin on clean lake with great deck and dock, holiday rental in Winchester
Cabin on clean lake with great deck and dock, holiday rental in Winchester

Cabin on clean lake with great deck and dock

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

Cozy Updated Log Cabin with Mountain Views close to Monadnock

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

Lake house getaway on pristine Spofford Lake, New Hampshire

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Downtown Hot Tub Escape, holiday rental in Winchester
Downtown Hot Tub Escape, holiday rental in Winchester
Downtown Hot Tub Escape, holiday rental in Winchester

Downtown Hot Tub Escape

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
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Picturesque Lakefront Retreat at Spofford Lake, holiday rental in Winchester
Picturesque Lakefront Retreat at Spofford Lake, holiday rental in Winchester
Picturesque Lakefront Retreat at Spofford Lake, holiday rental in Winchester

Picturesque Lakefront Retreat at Spofford Lake

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

Penthouse, Steps to the Sandy Beach & clear water

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

Waterfront House on Private Lake - Tranquil Location and Amazing Sunsets

Holiday Rental House
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, holiday rental in Winchester
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat, holiday rental in Winchester
Main House, Relax and enjoy the scenery, go and swim, fish or start your boat, holiday rental in Winchester

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
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Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford, holiday rental in Winchester
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford, holiday rental in Winchester
Tyler House, 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford, holiday rental in Winchester

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

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
More info
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Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, holiday rental in Winchester
Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, holiday rental in Winchester
Victorian Lakefront Cottage With Spectacular Sunrise View Of Water, holiday rental in Winchester

Victorian Lakefront Cottage With Spectacular Sunrise View Of Water

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

Monadnock 4-Bedroom Charmer by Cheshire Rail Trail

Holiday Rental House
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, holiday rental in Winchester
Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake, holiday rental in Winchester
Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake, holiday rental in Winchester

Charming 3 bedroom 2 bath Lakeside Cabin on Pristine Swanzey Lake

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

Historic Home w/ Modern Updates on < 4 Acres

Holiday Rental House
7 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Hillside Haven: Luxe Farm Escape with 5BR - 2 King Bed - 2 Full Bath - Sleeps 10, holiday rental in Winchester
Hillside Haven: Luxe Farm Escape with 5BR - 2 King Bed - 2 Full Bath - Sleeps 10, holiday rental in Winchester
Hillside Haven: Luxe Farm Escape with 5BR - 2 King Bed - 2 Full Bath - Sleeps 10, holiday rental in Winchester

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

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

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

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

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

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

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

Holiday Rental House
7 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Studio w/ Trail Access ~ 10 Mi to Brattleboro!, holiday rental in Winchester
Studio w/ Trail Access ~ 10 Mi to Brattleboro!, holiday rental in Winchester
Studio w/ Trail Access ~ 10 Mi to Brattleboro!, holiday 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., holiday rental in Winchester
Cozy Home Near Downtown, Shops, and Restaurants., holiday rental in Winchester
Cozy Home Near Downtown, Shops, and Restaurants., holiday rental in Winchester

Cozy Home Near Downtown, Shops, and Restaurants.

Holiday Rental House
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!, holiday rental in Winchester
Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!, holiday rental in Winchester
Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 10!, holiday rental in Winchester

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

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

Sauna and Mountain Views, the Perfect Cozy Vermont Getaway

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Cozy home in Brattleboro, holiday rental in Winchester
Cozy home in Brattleboro, holiday rental in Winchester
Cozy home in Brattleboro, holiday rental in Winchester

Cozy home in Brattleboro

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy 1-bedroom apartment in delightful Brattleboro, holiday rental in Winchester
Cozy 1-bedroom apartment in delightful Brattleboro, holiday rental in Winchester
Cozy 1-bedroom apartment in delightful Brattleboro, holiday 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, holiday rental in Winchester
The Covey House Retreat with InfraRed Sauna, holiday rental in Winchester
The Covey House Retreat with InfraRed Sauna, holiday 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, holiday rental in Winchester
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options, holiday rental in Winchester
RESTful yurt in charming Hinsdale; pet-friendly with multiple hiking options, holiday rental in Winchester

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

Holiday Rental House
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
More info
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Fully furnished/Pet Friendly!, holiday rental in Winchester
Fully furnished/Pet Friendly!, holiday rental in Winchester
Fully furnished/Pet Friendly!, holiday 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!, holiday rental in Winchester
Peaceful lake front home on beautiful Spofford Lake!, holiday rental in Winchester
Peaceful lake front home on beautiful Spofford Lake!, holiday rental in Winchester

Peaceful lake front home on beautiful Spofford Lake!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
More info
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Vikings Villages Resort - Double Bed Room, holiday rental in Winchester
Vikings Villages Resort - Double Bed Room, holiday rental in Winchester
Vikings Villages Resort - Double Bed Room, holiday rental in Winchester

Vikings Villages Resort - Double Bed Room

Holiday Rental House
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, holiday rental in Winchester
Charming 2BR semi-rural home in Southern VT - amazing setting & modern amenities, holiday rental in Winchester
Charming 2BR semi-rural home in Southern VT - amazing setting & modern amenities, holiday rental in Winchester

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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Cozy, Rustic Summer Cabin on Clean Lake, holiday rental in Winchester
Cozy, Rustic Summer Cabin on Clean Lake, holiday rental in Winchester
Cozy, Rustic Summer Cabin on Clean Lake, holiday rental in Winchester

Cozy, Rustic Summer Cabin on Clean Lake

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Fully furnished 2 bdr apartment, holiday rental in Winchester
Fully furnished 2 bdr apartment, holiday rental in Winchester
Fully furnished 2 bdr apartment, holiday 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, holiday rental in Winchester
Charming 3-bedroom farmhouse in fantastic Northfield with WiFi, AC, holiday rental in Winchester
Charming 3-bedroom farmhouse in fantastic Northfield with WiFi, AC, holiday rental in Winchester

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Showing results 1-44 of 44
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