Compare Winchester Cottage Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Winchester Cottages

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
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
$334 nightly
The price is $362 total per night
$362 total
Dec 1 - Dec 2
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
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
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
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
Historic Home w/ Modern Updates on < 4 Acres

Historic Home w/ Modern Updates on < 4 Acres

3 out of 5
Royalston MA
This cottage features free WiFi in public areas and barbecue grills. You can put free parking to good use if you drive.
Kitchen
Pet friendly
Cottage on Partridge Pond

Cottage on Partridge Pond

Westminster MA
Guests of this cottage enjoy access to a water park, laundry facilities, and barbecue grills.
Kitchen
Washer
Finnish Cabin with Sauna on Lake Monomonac

Finnish Cabin with Sauna on Lake Monomonac

2 out of 5
Rindge NH
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
Modern Waterfront Gem w/ Dock on Lake Monomonac

Modern Waterfront Gem w/ Dock on Lake Monomonac

3 out of 5
Winchendon MA
This cottage features free WiFi in public areas and barbecue grills. You can take advantage of free parking if you drive.
Kitchen
Parking included
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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 Dec 2 to Dec 3
    $161 total
    Dec 2 - Dec 3
    Total with taxes and fees
    8.8/10 Excellent! (1,004 reviews)
    Hampton Inn & Suites Greenfield

    Hampton Inn & Suites Greenfield

    184 Shelburne Rd Greenfield MA
    $183 nightly
    The price is $205 total per night from Dec 2 to Dec 3
    $205 total
    Dec 2 - Dec 3
    Total with taxes and fees
    8.6/10 Excellent! (873 reviews)
    Hampton Inn Brattleboro

    Hampton Inn Brattleboro

    1378 Putney Road Brattleboro VT
    $143 nightly
    The price is $158 total per night from Dec 3 to Dec 4
    $158 total
    Dec 3 - Dec 4
    Total with taxes and fees
    8.2/10 Very Good! (922 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
$158
Highest Price
$362
Popular accommodation
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly, 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock, Waterfront Cottage on Scenic Sportsman Pond, Lakeview Cozy Cottage • Hot Tub • Fireplace • Fish • Ski 30min, Vacationer's oasis on the waterfront of picturesque Pearly Pond., Historic Home w/ Modern Updates on < 4 Acres, Cottage on Partridge Pond, Finnish Cabin with Sauna on Lake Monomonac, Modern Waterfront Gem w/ Dock on Lake Monomonac

Explore More Ways to Travel with Travelocity