Compare Winchester Cottage Rentals

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Featured Cottages in Winchester

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
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
Jun 7 - Jun 8
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
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
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
Guests staying at this cottage have access to laundry facilities, a garden, and 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
$290 nightly
The price is $314 total per night
$314 total
Jun 8 - Jun 9
Total with taxes and fees
This cottage is a smoke-free cottage.
Kitchen
Air conditioning
Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe

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

Stoddard NH
At this cottage, guests have access to barbecue grills.
Kitchen
Free WiFi
Cavalier Cottage B&B

Cavalier Cottage B&B

3 out of 5
236 East Oxbow Road Shelburne Falls MA
This cottage features free WiFi in public areas, a terrace, and laundry facilities. If you drive, put free parking to good use. Additional amenities include a garden and a picnic area.
Breakfast included
Kitchen
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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

    2 private mountain RV pads for rent. Full hook ups

    2 private mountain RV pads for rent. Full hook ups

    Winchester NH
    $75 nightly
    The price is $81 total per night from Jun 7 to Jun 8
    $81 total
    Jun 7 - Jun 8
    Total with taxes and fees
    The Colonial Hotel

    The Colonial Hotel

    625 Betty Spring Road Gardner MA
    $170 nightly
    The price is $190 total per night from Jun 7 to Jun 8
    $190 total
    Jun 7 - Jun 8
    Total with taxes and fees
    8.8/10 Excellent! (1,003 reviews)
    Latchis Hotel

    Latchis Hotel

    50 Main Street Brattleboro VT
    $130 nightly
    The price is $143 total per night from Jun 7 to Jun 8
    $143 total
    Jun 7 - Jun 8
    Total with taxes and fees
    8.6/10 Excellent! (893 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
$81
Highest Price
$314
Popular accommodation
Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow, Waterfront Cottage on Scenic Sportsman Pond, Cabin & Sauna on Lake Monomonac near Mt. Monadnock, Vacationer's oasis on the waterfront of picturesque Pearly Pond., Cottage on Partridge Pond, 2 Bed, 1.5 Bath, on Pool Pond, Close to Franklin Pierce and Mt. Monadnock, Entire 3 Bedroom Cottage with lots of outdoor space 20 min to Brattleboro, Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe, Cavalier Cottage B&B

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