Vacation Homes in Winchester
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Featured Vacation Homes in Winchester

Lovely 2nd Floor Apartment

Beautiful Custom Built Timber Frame Home, Sleeps 11

Stylish remodeled 2 bedroom property in enchanting Shelburne Falls Village.

Charming Waterfront Log Cabin

Quiet Country 2 Bedroom Home Near Bellows Falls & Walpole — Easy I-91 Access

Nestled on the edge of the woods near Mount Monadnock

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Family Friendly Hilltop House In Putney Vermont

Luxury prop, Stunning views, private setting,pet friendly, fire pit ,WIFI,AC,EV

Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 12!

Peaceful riverfront house, dog-friendly, woodstove, decks, bbq, firepit, dock

1770 House - An end of a dirt road hideaway where you can relax and unwind.
Top trending hotels in Winchester

Vikings Villages Resort
Vacation Rentals in Winchester
What kind of vacation do you want in Winchester? The answer to that question will help you choose the right lodging for your stay. The wise wanderer knows that a vacation rental is an essential part of the traveling experience. It’s more than just a place to crash at night—it’s where you wake up in the morning, where you lounge when you’re not exploring, and it’s the starting point for all your adventures. No matter what type of vacation homes strike your fancy, Travelocity has something in Winchester that will speak to you.
Do you want a fully equipped kitchen so you can exercise your culinary mastery and impress your travel buddies? How about a romantic terrace for your anniversary trip? Have you always wished to fall asleep to the sound of waves crashing on the shore? One of our vacation home rentals is bound to add that extra magic to your trip. In fact, we’ve got plenty of options lined up just for you in Winchester, including luxury vacation rentals. On a budget? We can work with your funds and still give you a great place to sleep at night.
Take a look at what we have on offer. You’ll find rentals close to the big tourist draws, as well as rentals that keep you away from the crowd. Consider vacation rentals a little off the beaten path where you can live like a local and discover hidden gems that never make it to the tourist sites. Book through Travelocity and start your getaway today.
Winchester Vacation Homes essential information
Accommodation | 109 Vacation Homes |
|---|---|
Lowest Price | CA $145 |
Highest Price | CA $431 |
Popular accommodation | Lovely 2nd Floor Apartment, Beautiful Custom Built Timber Frame Home, Sleeps 11, Stylish remodeled 2 bedroom property in enchanting Shelburne Falls Village., Charming Waterfront Log Cabin, Quiet Country 2 Bedroom Home Near Bellows Falls & Walpole — Easy I-91 Access, Nestled on the edge of the woods near Mount Monadnock, Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns, Family Friendly Hilltop House In Putney Vermont, Luxury prop, Stunning views, private setting,pet friendly, fire pit ,WIFI,AC,EV, Spacious Pet Friendly Waterfront w/ Hot Tub & Yogo Studio-Sleeps 12!, Peaceful riverfront house, dog-friendly, woodstove, decks, bbq, firepit, dock, 1770 House - An end of a dirt road hideaway where you can relax and unwind. |





