Compare Windham Vacation Rentals

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Windham Rentals

A'Neils Windham Ski Lodge & Family Retreat

A'Neils Windham Ski Lodge & Family Retreat

2.79 mi from city center
This vacation home offers ski-in/ski-out access, an arcade/game room, and laundry facilities. Other amenities at this ski vacation home include a garden and barbecue grills.
Tiny House on Walnut Grove

Tiny House on Walnut Grove

2 out of 5
4.61 mi from city center
$236 nightly
The price is $255 total per night
$255 total
Oct 2 - Oct 3
Total with taxes and fees
Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills.
Tuscan Year Round Beauty - Pickleball Court - Full Winter Rental Availability

Tuscan Year Round Beauty - Pickleball Court - Full Winter Rental Availability

1.98 mi from city center
Guests staying at this vacation home enjoy access to a water park, a gym, and a hot tub. Other amenities at this family-friendly vacation home include an arcade/game room, laundry facilities, and local meal delivery service.
Jessie's Harvest House

Jessie's Harvest House

10.13 mi from city center
$179 nightly
The price is $189 total per night
$189 total
Oct 1 - Oct 2
Total with taxes and fees
Guests staying at this vacation home enjoy features like ski-in/ski-out access.
Stunning Catskills Cabin Getaway, facing BelleAyre

Stunning Catskills Cabin Getaway, facing BelleAyre

16.56 mi from city center
Guests of this chalet enjoy a hot tub, an arcade/game room, and laundry facilities. Other amenities at this family-friendly chalet include a garden and barbecue grills.
Hot Tub
Kitchen
Starlite Motel

Starlite Motel

2.5 out of 5
8722 Route 28, Big Indian, NY
16.7 mi from city center
$125 nightly
The price is $140 total per night
$140 total
Oct 1 - Oct 2
Total with taxes and fees
Guests staying at Starlite Motel enjoy free WiFi in public areas, a terrace, and a garden. If you plan to drive, free parking is available. Front-desk staff can help with tours or tickets, and provide local restaurant recommendations. Additional amenities include a picnic area, a vending machine, and barbecue grills.
Postcard Cabins Eastern Catskills

Postcard Cabins Eastern Catskills

2 out of 5
282 Cairo Junction Rd, Catskill, NY
16.01 mi from city center
$204 nightly
The price is $220 total per night
$220 total
Oct 1 - Oct 2
Total with taxes and fees
There's free parking if you drive.
HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

HotTub and 200Mbps WiFi; work from home paradise, Wonderful Belleayre Cabin

19.13 mi from city center
$235 nightly
The price is $259 total per night
$259 total
Oct 1 - Oct 2
Total with taxes and fees
This chalet features a hot tub and barbecue grills.
A Spectacular 50 Mile View of the Hudson Valley in all seasons

A Spectacular 50 Mile View of the Hudson Valley in all seasons

17.31 mi from city center
At this apartment, guests have access to a garden.
Sioux Tipi on Chloe's Lake

Sioux Tipi on Chloe's Lake

18.9 mi from city center
$130 nightly
The price is $146 total per night
$146 total
Oct 5 - Oct 6
Total with taxes and fees
Guests of this vacation home have access to designated smoking areas.
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

18.97 mi from city center
$145 nightly
The price is $162 total per night
$162 total
Oct 1 - Oct 2
Total with taxes and fees
At this cabin, guests have access to features like laundry facilities. This cabin also has barbecue grills.
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream

19.88 mi from city center
$280 nightly
The price is $314 total per night
$314 total
Oct 5 - Oct 6
Total with taxes and fees
At this cottage, guests have access to barbecue grills.
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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.

Windham Large Group Rentals

How to Book Vacation Rentals in Windham



🏠 What is the best price for Windham vacation rentals?

Windham vacation rentals range in price, starting at $140 per night.


🏠 What types of vacation rentals in Windham can I rent?

Orbitz offers a wide range of Windham rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Windham condo rentals.


🏠 Is it free to cancel my Windham vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Windham vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Windham. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Windham?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Windham apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Windham?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Windham package deals will get you even more savings.

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More to Explore