Find Hotels with Connecting Rooms in Windham, NY

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Check availability on Windham Hotels with Connecting Rooms

Our top choices for Windham hotels with connecting rooms

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Hotel Vienna

Hotel Vienna

Hotel Vienna
2.5 star property
Windham
9.4 out of 10, Exceptional, (718)
"Great place to stay with family room it's very clear 👌"
United States
jaisson
$149 nightly
The price is $161
Dec 14 - Dec 15
Total with taxes and fees
Hotel Vienna
Interior
The Haüs Windham

The Haüs Windham

The Haüs Windham
2.0 star property
Windham
8.6 out of 10, Excellent, (20)
"Very good"
United States
Sophia
$229 nightly
The price is $248
Dec 15 - Dec 16
Total with taxes and fees
The Haüs Windham
Suite, Multiple Beds (2 Queen Beds with Sofa bed) | Pillowtop beds, in-room safe, desk, iron/ironing board
Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Holiday Inn Express Hotel & Suites West Coxsackie by IHG
2.5 star property
West Coxsackie
8.4 out of 10, Very Good, (980)
"Perfect spot for an overnight stay when coming to the area"
United States
Lisa
$83 nightly
The price is $90
Jan 4 - Jan 5, 2026
Total with taxes and fees
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
Dinner served
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (822)
"Wonderful views, location, and accommodations. I would gladly return to Hunter Lodge"
United States
Russel
$168 nightly
The price is $182
Dec 15 - Dec 16
Total with taxes and fees
Hunter Lodge, a Bluebird by Lark
Indoor pool
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
2.0 star property
Saugerties
7.6 out of 10, Good, (1002)
"Easy check in, friendly staff. "
United States
Daniel
$104 nightly
The price is $116
Dec 14 - Dec 15
Total with taxes and fees
Howard Johnson by Wyndham Saugerties
Desk, blackout drapes, iron/ironing board, free WiFi
Red Ranch Motel

Red Ranch Motel

Red Ranch Motel
2.5 star property
Catskill
7.2 out of 10, Good, (485)
"The accommodations are pleasant, though the mattresses are quite firm, offering a sleeping experience reminiscent of a traditional box spring."
United States
Thoa
$107 nightly
The price is $115
Dec 14 - Dec 15
Total with taxes and fees
Red Ranch Motel
Interior detail
Urban Cowboy Lodge

Urban Cowboy Lodge

Urban Cowboy Lodge
5.0 star property
Big Indian
9.2 out of 10, Wonderful, (188)
" Didn’t get the room shown on Expedia website so we were disappointed in that. Overall nice place and really enjoyed our stay. "
United States
Stuart
$129 nightly
The price is $144
Jan 4 - Jan 5, 2026
Total with taxes and fees
Urban Cowboy Lodge
Exterior
Margaretville Mtn Inn B&B and Village Suites

Margaretville Mtn Inn B&B and Village Suites

Margaretville Mtn Inn B&B and Village Suites
3.0 star property
Margaretville
8.2 out of 10, Very Good, (206)
"Our stay at the Margaretville Mtn Inn was fantastic. The room was beautiful and very clean. The breakfast that was served was wholesome and delicious. I would definitely stay there again."
United States
Neal
$145 nightly
The price is $159
Jan 4 - Jan 5, 2026
Total with taxes and fees
Margaretville Mtn Inn B&B and Village Suites
Restaurant
Eastwind Oliverea Valley

Eastwind Oliverea Valley

Eastwind Oliverea Valley
2.0 star property
Big Indian
9.4 out of 10, Exceptional, (34)
"Very cozy for a weekend gateway "
United States
Fiorentin
$295 nightly
The price is $330
Dec 16 - Dec 17
Total with taxes and fees
Eastwind Oliverea Valley
Exterior
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
2.5 star property
Saugerties
8.8 out of 10, Excellent, (690)
"Clean rooms, very friendly and accommodating staff. Breakfast was very nice. Just overall wonderful hotel"
United States
Gideon
$125 nightly
The price is $140
Jan 11 - Jan 12, 2026
Total with taxes and fees
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
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.
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Top Windham Hotel Reviews

Hotel Vienna

Hotel Vienna

10/10 Excellent
"Love this place when its available. Low key, clean and conveniently near BOTH Hunter and Windham ski areas!"
Bruce 1-night trip
Posted 5 days ago
Hotel Vienna

Frequently asked questions

How much do hotels with connecting rooms in Windham cost?
The price range for hotels with connecting rooms in Windham is $90 to $330 per night. No matter your budget, you'll find something that suits your wallet — as well as your whole crew! These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Why book your hotel with connecting rooms in Windham with Expedia?
Getaways with the family should be stress-free, so if you're chasing hotels with connecting rooms at a competitive rate, Expedia has you covered. Keep costs down and check in to a low-cost motel with connecting rooms, or book a 5-star hotel and really spoil your crew. Our search filters make it simple to secure a stay in Windham that meets your needs.
How can I find cheap hotels with connecting rooms in Windham?
A great way to locate cheap hotels with connecting rooms in Windham is with Expedia's filter tool. Narrow your search results by budget, star rating and amenities to snag awesome bargains in just a few keystrokes.

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