
Vacation rentals in Winchester
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Top-rated vacation rentals in Winchester
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Popular amenities for Winchester vacation rentals
Winchester fishing vacation rentals

Cozy and Romantic Granite Lake Cottage Getaway

Beautiful Lakefront Log Cabin

The Lake Cottage: A Sweetwater Stay

Beautiful Log Cabin on Highland Lake

Lake Wyola House Shutesbury Massachusetts

Cozy Vermont Antique Sugar House with Fireplace

Newer Home on quiet 200 acre lake - sleeps 6

“Sugar Maple” Rustic Cabin Getaway with Fireplace
Lake side house rentals in Winchester

Wachusett Mountain Get-Away

Willow Falls Home ~Hot tub & Waterfront

The River House

The Grafton Chateau

MtSnow * HotTub * Pool * Air Hockey * PingPong * Darts

Lakefront, view of ski mtn, fireplace, sauna

Vermont Mirror House

Four Season Cozy Cottage on Lake Mattawa
Winchester fishing house rentals

J&J’s Retreat

The Boat House on Granite Lake

Vermont Village Retreat Near Mount Snow

Escape to the Lake!

Spacious Waterfront w/ Hot Tub & Yogo Studio

Harrisville Lake House - A Tranquil Get-Away

Gorgeous Vermont Lakefront with epic sunsets!

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- Stratton Mountain
- Okemo Mountain Resort
- Monadnock State Park
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Pats Peak Ski Area
- Brimfield State Forest
- Manchester Country Club - NH
- Mount Greylock Ski Club
- Mount Snow Ski Resort
- The Shattuck Golf Club
- Nashoba Valley Winery, Distillery, Brewery and Restaurant
- Magic Mountain Ski Resort
- Stratton Mountain Resort
- Nashua Country Club
- Bright Nights at Forest Park
- Hildene, The Lincoln Family Home
- Dorset Field Club
- Bromley Mountain Ski Resort
- Mount Sugarloaf State Reservation
- Clarksburg State Park
- Mount Tom State Reservation
- Bretwood Golf Course
- Fox Run Golf Club
- Family travel hub Tips and inspiration
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- Outdoor adventure Explore nature with the family
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- Kid-friendly state parks Check out these family-friendly hikes