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, a garden, and barbecue grills.
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 a garden. This smoke-free cottage also has barbecue grills.
Hot Tub
Kitchen
Waterfront Cottage on Scenic Sportsman Pond

Waterfront Cottage on Scenic Sportsman Pond

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

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Rindge NH
$253 nightly
The price is $275 total per night
$275 total
Apr 21 - Apr 22
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, a water dispenser, and barbecue grills.
Kitchen
Washer
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
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
2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock

Rindge NH
$330 nightly
The price is $358 total per night
$358 total
Apr 22 - Apr 23
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
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 a garden. This smoke-free 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
$226 nightly
The price is $246 total per night
$246 total
Apr 21 - Apr 22
Total with taxes and fees
This cottage is a smoke-free cottage.
Kitchen
Air conditioning
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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
    $144 nightly
    The price is $161 total per night from Apr 21 to Apr 22
    $161 total
    Apr 21 - Apr 22
    Total with taxes and fees
    8.8/10 Excellent! (1,003 reviews)
    Colonial Motel And Spa

    Colonial Motel And Spa

    889 Putney Rd Brattleboro VT
    6.8/10 (1,003 reviews)
    Hampton Inn Brattleboro

    Hampton Inn Brattleboro

    1378 Putney Road Brattleboro VT
    $107 nightly
    The price is $118 total per night from Apr 27 to Apr 28
    $118 total
    Apr 27 - Apr 28
    Total with taxes and fees
    8.2/10 Very Good! (963 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
54 Cottages
Lowest Price
$118
Highest Price
$358
Popular accommodation
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly, Lakeview Cozy Cottage • Hot Tub • Fireplace • Fish • Ski 30min, Waterfront Cottage on Scenic Sportsman Pond, Cabin & Sauna on Lake Monomonac near Mt. Monadnock, Cottage on Partridge Pond, Vacationer's oasis on the waterfront of picturesque Pearly Pond., 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock, Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow, Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro

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