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 barbecue grills and a garden.
Kitchen
Washer
Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Rindge NH
$280 nightly
The price is $304 total per night
$304 total
Sep 17 - Sep 18
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 barbecue grills, a garden, and a water dispenser.
Kitchen
Washer
2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce

Rindge NH
$361 nightly
The price is $392 total per night
$392 total
Sep 10 - Sep 11
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
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
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 Lake Nubanusit

Cottage Lake Nubanusit

Nelson NH
At this cottage, guests have access to barbecue grills.
Kitchen
Free WiFi
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
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
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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 Sep 10 to Sep 11
    $81 total
    Sep 10 - Sep 11
    Total with taxes and fees
    Latchis Hotel

    Latchis Hotel

    50 Main Street Brattleboro VT
    $123 nightly
    The price is $135 total per night from Sep 10 to Sep 11
    $135 total
    Sep 10 - Sep 11
    Total with taxes and fees
    8.6/10 Excellent! (977 reviews)
    Colonial Motel

    Colonial Motel

    889 Putney Rd Brattleboro VT
    $84 nightly
    The price is $93 total per night from Sep 10 to Sep 11
    $93 total
    Sep 10 - Sep 11
    Total with taxes and fees
    6.6/10 (54 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
51 Cottages
Lowest Price
$81
Highest Price
$392
Popular accommodation
Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly, Cabin & Sauna on Lake Monomonac near Mt. Monadnock, 2 Bed 1.5 Bath on Pool Pond Close Franklin Pierce, Beautiful Vacation Cottage with a View in Newfane, Vermont, near Mt. Snow, Waterfront Cottage on Scenic Sportsman Pond, Vacationer's oasis on the waterfront of picturesque Pearly Pond., Cottage Lake Nubanusit, Lakeside living! Relax and enjoy prestine Granite Lake…..your oasis to breathe, Cottage on Partridge Pond

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