We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Winchester Vacation Rentals

List your property
Owner log in
Where to?
Check in
— / — / —
Check out
— / — / —
Guests
0 rooms, 2+ guests

Bedrooms

Bathrooms

Amenities

Suitability

Property type

Distinctive Features

Distance from

1 mi
50 rentals in Winchester.
Sort by:
Tripadvisor Sort
Revenue impacts this sort order. Learn more.
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
More info
Vrbo.com logo
Check in
Check out

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
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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
More info
Check in
Check out
Payment Protection

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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
More info
Check in
Check out
Payment Protection

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
More info
Vrbo.com logo
Check in
Check out

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
Vrbo.com logo
Check in
Check out

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Save time - get the best Winchester rentals sent straight to your email!
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
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 9
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Amazing Mid-Century Modern Mountain Top Home on 160 Acres, vacation rental in Winchester
Amazing Mid-Century Modern Mountain Top Home on 160 Acres, vacation rental in Winchester
Amazing Mid-Century Modern Mountain Top Home on 160 Acres, vacation rental in Winchester

Amazing Mid-Century Modern Mountain Top Home on 160 Acres

Rental Home
6 bedrooms
6 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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!

Rental Home
8 bedrooms
9 bathrooms
Sleeps 15
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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
More info
Vrbo.com logo
Check in
Check out

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 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Charming Pet-friendly studio w/fireplace, vacation rental in Winchester
Charming Pet-friendly studio w/fireplace, vacation rental in Winchester
Charming Pet-friendly studio w/fireplace, vacation rental in Winchester

Charming Pet-friendly studio w/fireplace

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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 3
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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
More info
Vrbo.com logo
Check in
Check out

NEW! 'Fiddler's Rest:' Cabin 11 Miles to Skiing, vacation rental in Winchester
NEW! 'Fiddler's Rest:' Cabin 11 Miles to Skiing, vacation rental in Winchester
NEW! 'Fiddler's Rest:' Cabin 11 Miles to Skiing, vacation rental in Winchester

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

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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!

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Off-Grid  Camp,  Lakeside Cottage, vacation rental in Winchester
Off-Grid  Camp,  Lakeside Cottage, vacation rental in Winchester
Off-Grid  Camp,  Lakeside Cottage, vacation rental in Winchester

Off-Grid Camp, Lakeside Cottage

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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!

Rental Home
3 bedrooms
4 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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
Vrbo.com logo
Check in
Check out

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
More info
Check in
Check out
Payment Protection

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
More info
Vrbo.com logo
Check in
Check out

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
2 bathrooms
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
More info
Check in
Check out
Payment Protection

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection

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
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection

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 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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!

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
3 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Cozy Cottage along Idyllic Green River, vacation rental in Winchester
Cozy Cottage along Idyllic Green River, vacation rental in Winchester
Cozy Cottage along Idyllic Green River, vacation rental in Winchester

Cozy Cottage along Idyllic Green River

Rental Home
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

House, vacation rental in Winchester
House, vacation rental in Winchester
House, vacation rental in Winchester

House

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection

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
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

Stunning LAKESIDE Guesthouse, vacation rental in Winchester
Stunning LAKESIDE Guesthouse, vacation rental in Winchester
Stunning LAKESIDE Guesthouse, vacation rental in Winchester

Stunning LAKESIDE Guesthouse

Rental Home
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out

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
More info
Vrbo.com logo
Check in
Check out

PreviousNext
1
Frequently Asked Questions about Winchester