Winchester Apartments

Name: Cozy apt in beautiful secluded spot 15 mins from Mt Snow
Address: Dover
Price range: $205 total

Featured Apartments in Winchester

Riverside Retreat – Cozy 2-Story Getaway!

At this apartment, guests have access to barbecue grills.

Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.

$169 nightly

$183 total

Oct 6 - Oct 7

Total with taxes and fees

At this apartment, guests have access to barbecue grills.

Spacious & Cozy Ground Floor 2/3 Bed private suite

$321 nightly

$358 total

Oct 5 - Oct 6

Total with taxes and fees

This apartment is a smoke-free apartment building.

At this apartment, guests have access to barbecue grills.

Lake Whitingham & Mount Snow Area Village Apartment

$272 nightly

$305 total

Oct 6 - Oct 7

Total with taxes and fees

Guests staying at this apartment have access to barbecue grills and a garden.

Charming 1-bedroom apartment with WiFi, AC in delightful Brattleboro

This apartment is a smoke-free apartment building.

Walk to Trails: Artsy Mtn-view Getaway in Vernon!

Guests of this apartment enjoy features like free WiFi in public areas. You can put free parking to good use if you drive.

HeART Barn, 35-60 m. to skiing @ Mt. Snow, Stratton, Okemo, Magic & Bromley

At this apartment, guests have access to barbecue grills.

Cozy apt in beautiful secluded spot 15 mins from Mt Snow

$181 nightly

$205 total

Oct 31 - Nov 1

Total with taxes and fees

This apartment is a smoke-free apartment building.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Hotel Options in Winchester

The Colonial Hotel

625 Betty Spring Road, Gardner, MA

$160 nightly

$179 total

Oct 20 - Oct 21

Total with taxes and fees

8.8/10 Excellent! (1,016 reviews)

Econo Lodge Brattleboro

515 Canal St, Brattleboro, VT

$68 nightly

$75 total

Nov 2 - Nov 3

Total with taxes and fees

5.4/10 (568 reviews)

Keene Elm City Hotel, an Ascend Collection Hotel

175 Key Rd, Keene, NH

$107 nightly

$116 total

Nov 2 - Nov 3

Total with taxes and fees

8.4/10 Very Good! (908 reviews)

Apartments

Book apartments in Winchester

Find your home-away-from-home when you book your next stay at an apartment in Winchester. Apartments are ideal for families, groups of friends and even solo travelers. More space, more options and more freedom—apartments are short-term digs that feel like a long-term arrangement. From one-bedroom apartments to three bedrooms or more, Orbitz has an incredible selection to choose from. It’s never been easier to live like a local in Winchester.

Apartments for everyone in Winchester
Family apartments in Winchester have plenty of room for everyone. You’ll find multiple bedrooms, laundry facilities and furnished living rooms, so you can have movie nights just like at home. Plus, hotels with kitchens cut down on time spent finding kid-friendly restaurants. Spend that time making memories instead.

Friends are the family you choose, but you don’t need to be too close this vacation. Luckily, you can book apartments even your pickiest pal will love. This getaway with the girls or guys doesn’t have to break the bank, either. Cheap apartments in Winchester are just a click away. When it comes time to split the bill, no one will bail.

If you want the finer things in life, we’ll help you find luxury apartments in Winchester faster than you can say “thousand thread count sheets.” Get your best sleep ever, then wake up with a freshly brewed espresso and a full breakfast. It’s just like home, only much, much better.

Whether you’re a bargain hunter or a luxury lover, kitchens and kitchenettes are one of the most important features of short-term apartments in Winchester. It’s simple, really: Cooking your own meals is downright convenient. Even if you’re not a five-star chef, late-night snacks and morning mimosas get a whole lot easier when you’ve got a fully stocked kitchen to play with.