Holiday Homes in Winchester
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50 rentals in Winchester.
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Stay at a Craft Brewery in Winchester NH Close to mountains, hiking, & breweries
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Magical Lakefront Home on Forest Lake
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
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Beautiful Lake Side Getaway, Quiet, and Peaceful
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 6
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Stay at a Craft Brewery
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Stunning Forest Lake Home with Hot Tub open all Yr
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 10
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Lakefront Retreat in Winchester, Getaway Ready and Fully Equipped
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
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Large modern house with huge open great room and four large bedrooms with baths
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Serenity Cottage in Southern Vermont…
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Sprawling, secluded gourmand's large cottage at base of Mt Monadnock
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
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Peaceful, Beautiful, Comfortable Modern Cape With Mountain Views
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Save time - get the best Winchester rentals sent straight to your email!
The Comforts of Home...
Holiday Rental House
3 bedrooms
0 bathrooms
Sleeps 8
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Beautiful lakefront log home nestled in the pines
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Secluded Architect designed House - Monadnock Region - Great Escape
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Romantic Rock River Cottage with Hot Tub, Fireplace & Beach - Newfane VT
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
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Charming Lakeside Cabin on Pristine Swanzey Lake
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Laurel Lake Cottage in New Hampshire
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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3 BR Farmhouse on 100 Acre Farm Near Vermont
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Pet And Family Friendly Hilltop House In Putney Vermont
Holiday Rental House
0 bedrooms
2 bathrooms
Sleeps 8
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The Fishing Cottage, A Sweetwater Stay
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 5
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Tyler House - 4 Bedrooms, 2 Bathrooms, House to steps to Lake Spofford
Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 12
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Vacationer's oasis on the waterfront of picturesque Pearly Pond.
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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Spacious Lakeside Waterfront Summer Cottage
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
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Quiet Vermont Home Close To Everything
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Lakefront all-season beauty and fun!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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Vermont Log Cabin available for weekend and weekly
Cabin Holiday Rental
2 bedrooms
1 bathroom
Sleeps 5
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Escape to peaceful Putney Vermont
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
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Main House - Relax and enjoy the scenery, go and swim, fish or start your boat
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 9
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Cozy Waterfront Cottage Only Minutes from Downtown Keene, NH!
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Hilltop Home with Great Views
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Cozy, pet-friendly one-bedroom apartment in Brattleboro, Vermont
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
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Large home for families or groups
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront New Englander Mt. Monadnock
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 7
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Penthouse - Steps to the Sandy Beach & clear water
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Serene Shelburne Studio Cabin w/Spring-Fed Pool!
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Lake house getaway on pristine Spofford Lake, New Hampshire
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Skywood - - Dublin, NH
Holiday Rental House
8 bedrooms
6 bathrooms
Sleeps 13
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PARADISE on EARTH! - Historic 4BR Farmhouse
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Marlboro, Vermont Ski House - discount offered
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Victorian Lakefront Cottage With Spectacular Sunrise View Of Water
Holiday Rental House
4 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
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A Healing Forest Space in the Heart of New England
Condo/Apartment
0 bedrooms
1 bathroom
Sleeps 4
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Church sanctuary
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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Lakeside Lodge with Rock Fireplace
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Fully Furnished/Pet Friendly!
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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Renovated Cottage w/spectacular mountain view
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Studio - Cozy Studio for 2 or 4!
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 2
Match: Sleeps
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PoshHaus Court ST Colonial
Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Jabulani Luxury Rural Stay
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Bellows Cottage at The Inn at Valley Farms
Holiday Rental House
3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Picturesque Lakefront Retreat at Spofford Lake, Sleeps 10
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Hemlock House at Aldworth Manor
Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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1
Frequently Asked Questions about Winchester
- Yes, here are some popular holiday rentals in Winchester that have a pool:\n
- \n
- Beautiful Lake Side Getaway, Quiet, and Peaceful \n
- Stunning Forest Lake Home with Hot Tub open all Yr \n
- Stay at a Craft Brewery \n
- Yes, here are some popular holiday rentals in Winchester that have internet access:\n
- \n
- Beautiful Lake Side Getaway, Quiet, and Peaceful \n
- Stunning Forest Lake Home with Hot Tub open all Yr \n
- Magical Lakefront Home on Forest Lake \n
- The best pet friendly rentals in Winchester are:\n
- \n
- Stunning Forest Lake Home with Hot Tub open all Yr \n
- Stay at a Craft Brewery \n
- Lakefront Retreat in Winchester, Getaway Ready and Fully Equipped \n
- Some of the most popular kid friendly rentals in Winchester are:\n
- \n
- Stunning Forest Lake Home with Hot Tub open all Yr \n
- Magical Lakefront Home on Forest Lake \n
- Beautiful Lake Side Getaway, Quiet, and Peaceful \n