Compare Winchester Cottage Rentals

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Featured Winchester Cottages

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

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

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
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

Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe

Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe

$526 nightly
The price is $571 total per night
$571 total
Oct 8 - Oct 9
Total with taxes and fees
At this cottage, guests have access to barbecue grills.
Kitchen
Free WiFi
Waterfront Cottage on Scenic Sportsman Pond

Waterfront Cottage on Scenic Sportsman Pond

Guests staying at this cottage have access to barbecue grills and a garden.
Vacationer's oasis on the waterfront of picturesque Pearly Pond.

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

At this cottage, guests have access to features like laundry facilities. This beach cottage also has barbecue grills.
Historic Home w/ Modern Updates on < 4 Acres

Historic Home w/ Modern Updates on < 4 Acres

3 out of 5
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

Guests of this cottage enjoy access to a water park, laundry facilities, and 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

$332 nightly
The price is $360 total per night
$360 total
Oct 5 - Oct 6
Total with taxes and fees
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!

Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!

Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
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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 Oct 20 to Oct 21
    $179 total
    Oct 20 - Oct 21
    Total with taxes and fees
    8.8/10 Excellent! (1,016 reviews)
    Econo Lodge Brattleboro

    Econo Lodge Brattleboro

    515 Canal St, Brattleboro, VT
    $68 nightly
    The price is $75 total per night from Nov 2 to Nov 3
    $75 total
    Nov 2 - Nov 3
    Total with taxes and fees
    5.4/10 (568 reviews)
    Keene Elm City Hotel, an Ascend Collection Hotel

    Keene Elm City Hotel, an Ascend Collection Hotel

    175 Key Rd, Keene, NH
    $107 nightly
    The price is $116 total per night from Nov 2 to Nov 3
    $116 total
    Nov 2 - Nov 3
    Total with taxes and fees
    8.4/10 Very Good! (908 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
53 Cottages
Lowest Price
$75
Highest Price
$571
Popular accommodation
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow, Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly, Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe, Waterfront Cottage on Scenic Sportsman Pond, Vacationer's oasis on the waterfront of picturesque Pearly Pond., Historic Home w/ Modern Updates on < 4 Acres, Cottage on Partridge Pond, 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock, Beautiful Waterfront Cottage With a HOT TUB For Your Family Getaway!

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