Compare Winchester Cottage Rentals

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Featured Cottages in Winchester

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Wilmington VT
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Lakeview Cozy Cottage • Hot Tub • Fireplace • Fish • Ski 30min

Lakeview Cozy Cottage • Hot Tub • Fireplace • Fish • Ski 30min

Rindge NH
Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Hot Tub
Kitchen
Cottage on Partridge Pond

Cottage on Partridge Pond

Westminster MA
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
Waterfront Cottage on Scenic Sportsman Pond

Waterfront Cottage on Scenic Sportsman Pond

Fitzwilliam NH
Guests staying at this cottage have access to barbecue grills and a garden.
Kitchen
Pet friendly
Finnish Cabin with Sauna on Lake Monomonac

Finnish Cabin with Sauna on Lake Monomonac

2 out of 5
Rindge NH
$241 nightly
The price is $262 total per night
$262 total
Mar 8 - Mar 9
Total with taxes and fees
Guests of this cottage enjoy features like a gym, a sauna, and laundry facilities. Other amenities at this beach cottage include a garden, barbecue grills, and a water dispenser.
Kitchen
Washer
Vacationer's oasis on the waterfront of picturesque Pearly Pond.

Vacationer's oasis on the waterfront of picturesque Pearly Pond.

Rindge NH
At this cottage, guests have access to features like laundry facilities. This beach cottage also has barbecue grills.
Kitchen
Washer
Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

Walpole NH
$244 nightly
The price is $265 total per night
$265 total
Mar 8 - Mar 9
Total with taxes and fees
This cottage is a smoke-free cottage.
Kitchen
Air conditioning
10 Mi to Mt Snow! Grand Estate Built to Entertain

10 Mi to Mt Snow! Grand Estate Built to Entertain

3 out of 5
Wilmington VT
This cottage features free WiFi in public areas and barbecue grills. A stay here includes free parking.
Kitchen
Washer
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

Newfane VT
Guests staying at this cottage enjoy free WiFi in public areas, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Kitchen
Washer
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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

    The Colonial Hotel

    625 Betty Spring Road Gardner MA
    $160 nightly
    The price is $179 total per night from Mar 8 to Mar 9
    $179 total
    Mar 8 - Mar 9
    Total with taxes and fees
    8.8/10 Excellent! (1,007 reviews)
    Colonial Motel And Spa

    Colonial Motel And Spa

    889 Putney Rd Brattleboro VT
    $100 nightly
    The price is $110 total per night from Mar 8 to Mar 9
    $110 total
    Mar 8 - Mar 9
    Total with taxes and fees
    6.8/10 (1,005 reviews)
    Hampton Inn Brattleboro

    Hampton Inn Brattleboro

    1378 Putney Road Brattleboro VT
    $106 nightly
    The price is $116 total per night from Mar 11 to Mar 12
    $116 total
    Mar 11 - Mar 12
    Total with taxes and fees
    8.2/10 Very Good! (948 reviews)

Cottages

Book a cottage in Winchester
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Winchester. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Winchester better.

Cottage apartments in Winchester range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Winchester
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Winchester and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Winchester cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Winchester. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Winchester Cottages essential information

Accommodation
58 Cottages
Lowest Price
$110
Highest Price
$265
Popular accommodation
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly, Lakeview Cozy Cottage • Hot Tub • Fireplace • Fish • Ski 30min, Cottage on Partridge Pond, Waterfront Cottage on Scenic Sportsman Pond, Finnish Cabin with Sauna on Lake Monomonac, Vacationer's oasis on the waterfront of picturesque Pearly Pond., Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro, 10 Mi to Mt Snow! Grand Estate Built to Entertain, Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow

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