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Winchester Pet Friendly Vacation Rentals

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21 rentals in Winchester.
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Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries, vacation rental in Winchester
Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries, vacation rental in Winchester
Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries, vacation rental in Winchester

Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Pet friendly
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Magical Lakefront Home on Forest Lake, vacation rental in Winchester
Magical Lakefront Home on Forest Lake, vacation rental in Winchester
Magical Lakefront Home on Forest Lake, vacation rental in Winchester

Magical Lakefront Home on Forest Lake

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps, Pet friendly
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Waterfront Cottage/Breathtaking View/10min from Keene NH /90min from Hartford CT, vacation rental in Winchester
Waterfront Cottage/Breathtaking View/10min from Keene NH /90min from Hartford CT, vacation rental in Winchester
Waterfront Cottage/Breathtaking View/10min from Keene NH /90min from Hartford CT, vacation rental in Winchester

Waterfront Cottage/Breathtaking View/10min from Keene NH /90min from Hartford CT

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps, Pet friendly
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Stay at a Craft Brewery, vacation rental in Winchester
Stay at a Craft Brewery, vacation rental in Winchester
Stay at a Craft Brewery, vacation rental in Winchester

Stay at a Craft Brewery

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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Downtown Loft above Winery and Distillery, vacation rental in Winchester
Downtown Loft above Winery and Distillery, vacation rental in Winchester
Downtown Loft above Winery and Distillery, vacation rental in Winchester

Downtown Loft above Winery and Distillery

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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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
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Lake Side Getaway, Quiet, and Peaceful, vacation rental in Winchester
Beautiful Lake Side Getaway, Quiet, and Peaceful, vacation rental in Winchester
Beautiful Lake Side Getaway, Quiet, and Peaceful, vacation rental in Winchester

Beautiful Lake Side Getaway, Quiet, and Peaceful

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Lakefront Cottage with Gorgeous Views, vacation rental in Winchester
Beautiful Lakefront Cottage with Gorgeous Views, vacation rental in Winchester
Beautiful Lakefront Cottage with Gorgeous Views, vacation rental in Winchester

Beautiful Lakefront Cottage with Gorgeous Views

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
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The Fishing Cottage, A Sweetwater Stay, vacation rental in Winchester
The Fishing Cottage, A Sweetwater Stay, vacation rental in Winchester
The Fishing Cottage, A Sweetwater Stay, vacation rental in Winchester

The Fishing Cottage, A Sweetwater Stay

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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Artsy, Pet-friendly studio w/fireplace, vacation rental in Winchester
Artsy, Pet-friendly studio w/fireplace, vacation rental in Winchester
Artsy, Pet-friendly studio w/fireplace, vacation rental in Winchester

Artsy, Pet-friendly studio w/fireplace

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps, Pet friendly
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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!

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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Waterfront Haven near Mount Monadnock. Pristine Lake, Mountain View & Sunsets!, vacation rental in Winchester
Waterfront Haven near Mount Monadnock. Pristine Lake, Mountain View & Sunsets!, vacation rental in Winchester
Waterfront Haven near Mount Monadnock. Pristine Lake, Mountain View & Sunsets!, vacation rental in Winchester

Waterfront Haven near Mount Monadnock. Pristine Lake, Mountain View & Sunsets!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps, Pet friendly
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Pet Friendly, Immaculate, updated, walkable to all Main St. & local parks!, vacation rental in Winchester
Pet Friendly, Immaculate, updated, walkable to all Main St. & local parks!, vacation rental in Winchester
Pet Friendly, Immaculate, updated, walkable to all Main St. & local parks!, vacation rental in Winchester

Pet Friendly, Immaculate, updated, walkable to all Main St. & local parks!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Pet friendly
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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

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps, Pet friendly
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A Healing Forest Space in the Heart of New England, vacation rental in Winchester
A Healing Forest Space in the Heart of New England, vacation rental in Winchester
A Healing Forest Space in the Heart of New England, vacation rental in Winchester

A Healing Forest Space in the Heart of New England

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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Cozy, pet-friendly one-bedroom apartment in Brattleboro, Vermont, vacation rental in Winchester
Cozy, pet-friendly one-bedroom apartment in Brattleboro, Vermont, vacation rental in Winchester
Cozy, pet-friendly one-bedroom apartment in Brattleboro, Vermont, vacation rental in Winchester

Cozy, pet-friendly one-bedroom apartment in Brattleboro, Vermont

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps, Pet friendly
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Serenity Cottage in Southern Vermont…, vacation rental in Winchester
Serenity Cottage in Southern Vermont…, vacation rental in Winchester
Serenity Cottage in Southern Vermont…, vacation rental in Winchester

Serenity Cottage in Southern Vermont…

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps, Pet friendly
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Sprawling, secluded gourmand's large cottage at base of Mt Monadnock, vacation rental in Winchester
Sprawling, secluded gourmand's large cottage at base of Mt Monadnock, vacation rental in Winchester
Sprawling, secluded gourmand's large cottage at base of Mt Monadnock, vacation rental in Winchester

Sprawling, secluded gourmand's large cottage at base of Mt Monadnock

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps, Pet friendly
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PoshHaus Court ST Colonial, vacation rental in Winchester
PoshHaus Court ST Colonial, vacation rental in Winchester
PoshHaus Court ST Colonial, vacation rental in Winchester

PoshHaus Court ST Colonial

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps, Pet friendly
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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

Holiday Rental House
6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
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Cottage on Laurel Lake, Private lake access, picture perfect sunsets, vacation rental in Winchester
Cottage on Laurel Lake, Private lake access, picture perfect sunsets, vacation rental in Winchester
Cottage on Laurel Lake, Private lake access, picture perfect sunsets, vacation rental in Winchester

Cottage on Laurel Lake, Private lake access, picture perfect sunsets

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps, Pet friendly
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House, vacation rental in Winchester
House, vacation rental in Winchester
House, vacation rental in Winchester

House

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps, Pet friendly
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The Cottage at Skycroft Farm  - 4 season respite and restoration, vacation rental in Winchester
The Cottage at Skycroft Farm  - 4 season respite and restoration, vacation rental in Winchester
The Cottage at Skycroft Farm  - 4 season respite and restoration, vacation rental in Winchester

The Cottage at Skycroft Farm - 4 season respite and restoration

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps, Pet friendly
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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

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps, Pet friendly
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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

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
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

Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 12
Match: Sleeps
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Spacious Lakeside Waterfront Summer Cottage, vacation rental in Winchester
Spacious Lakeside Waterfront Summer Cottage, vacation rental in Winchester
Spacious Lakeside Waterfront Summer Cottage, vacation rental in Winchester

Spacious Lakeside Waterfront Summer Cottage

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Lakeside Waterfront Cottage with Private Beach, vacation rental in Winchester
Beautiful Lakeside Waterfront Cottage with Private Beach, vacation rental in Winchester
Beautiful Lakeside Waterfront Cottage with Private Beach, vacation rental in Winchester

Beautiful Lakeside Waterfront Cottage with Private Beach

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Wonderful Private Home In West Brattleboro Off Of Route 9, vacation rental in Winchester
Wonderful Private Home In West Brattleboro Off Of Route 9, vacation rental in Winchester
Wonderful Private Home In West Brattleboro Off Of Route 9, vacation rental in Winchester

Wonderful Private Home In West Brattleboro Off Of Route 9

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Cozy Waterfront Cottage Only Minutes from Downtown Keene, NH!, vacation rental in Winchester
Cozy Waterfront Cottage Only Minutes from Downtown Keene, NH!, vacation rental in Winchester
Cozy Waterfront Cottage Only Minutes from Downtown Keene, NH!, vacation rental in Winchester

Cozy Waterfront Cottage Only Minutes from Downtown Keene, NH!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Jabulani Luxury Rural Stay, vacation rental in Winchester
Jabulani Luxury Rural Stay, vacation rental in Winchester
Jabulani Luxury Rural Stay, vacation rental in Winchester

Jabulani Luxury Rural Stay

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
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Spacious Estate w/ Courtyard: 2 Miles to Downtown!, vacation rental in Winchester
Spacious Estate w/ Courtyard: 2 Miles to Downtown!, vacation rental in Winchester
Spacious Estate w/ Courtyard: 2 Miles to Downtown!, vacation rental in Winchester

Spacious Estate w/ Courtyard: 2 Miles to Downtown!

Holiday Rental House
8 bedrooms
9 bathrooms
Sleeps 15
Match: Sleeps
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Charming Waterfront Log Cabin w/ Private Island, vacation rental in Winchester
Charming Waterfront Log Cabin w/ Private Island, vacation rental in Winchester
Charming Waterfront Log Cabin w/ Private Island, vacation rental in Winchester

Charming Waterfront Log Cabin w/ Private Island

Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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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

Holiday Rental House
3 bedrooms
2 bathrooms
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

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Rustic Cottage on Swanzey Lake with dock & firepit, vacation rental in Winchester
Rustic Cottage on Swanzey Lake with dock & firepit, vacation rental in Winchester
Rustic Cottage on Swanzey Lake with dock & firepit, vacation rental in Winchester

Rustic Cottage on Swanzey Lake with dock & firepit

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
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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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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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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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
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Jabulani Luxury Rural Stay, vacation rental in Winchester
Jabulani Luxury Rural Stay, vacation rental in Winchester
Jabulani Luxury Rural Stay, vacation rental in Winchester

Jabulani Luxury Rural Stay

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
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

Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Romantic, Tranquil Guest House - Peaceful Sanctuary plus Sauna, vacation rental in Winchester
Romantic, Tranquil Guest House - Peaceful Sanctuary plus Sauna, vacation rental in Winchester
Romantic, Tranquil Guest House - Peaceful Sanctuary plus Sauna, vacation rental in Winchester

Romantic, Tranquil Guest House - Peaceful Sanctuary plus Sauna

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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NEW! Tasteful Country Home on 5 Acres: Hike, Ski!, vacation rental in Winchester
NEW! Tasteful Country Home on 5 Acres: Hike, Ski!, vacation rental in Winchester
NEW! Tasteful Country Home on 5 Acres: Hike, Ski!, vacation rental in Winchester

NEW! Tasteful Country Home on 5 Acres: Hike, Ski!

Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Garden View In-Town Retreat w/ Trail Access, vacation rental in Winchester
Garden View In-Town Retreat w/ Trail Access, vacation rental in Winchester
Garden View In-Town Retreat w/ Trail Access, vacation rental in Winchester

Garden View In-Town Retreat w/ Trail Access

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Spacious Modern House, Beautiful Deck/Patio Overlooking Golf Course & Mountains, vacation rental in Winchester
Spacious Modern House, Beautiful Deck/Patio Overlooking Golf Course & Mountains, vacation rental in Winchester
Spacious Modern House, Beautiful Deck/Patio Overlooking Golf Course & Mountains, vacation rental in Winchester

Spacious Modern House, Beautiful Deck/Patio Overlooking Golf Course & Mountains

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Stunning LAKESIDE Guesthouse, vacation rental in Winchester
Stunning LAKESIDE Guesthouse, vacation rental in Winchester
Stunning LAKESIDE Guesthouse, vacation rental in Winchester

Stunning LAKESIDE Guesthouse

Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Uniquely Styled Private Studio with Coded Locks, vacation rental in Winchester
Uniquely Styled Private Studio with Coded Locks, vacation rental in Winchester
Uniquely Styled Private Studio with Coded Locks, vacation rental in Winchester

Uniquely Styled Private Studio with Coded Locks

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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