Compare Windham Guest House Rentals
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured Guest Houses in Windham
The Herwood Inn
148 Tinker St Woodstock NY
$144 nightly
The price is $162 total per night
$162 total
Jan 20 - Jan 21, 2026
Total with taxes and fees
At The Herwood Inn, guests have access to free WiFi in public areas, a hot tub, and free use of bicycles. Free parking is available if you drive. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this luxury guesthouse include express check-out, a terrace, and a gift shop.
Hot Tub
Pet friendly
Shadowcrest
973 Main St Fleischmanns NY
$180 nightly
The price is $198 total per night
$198 total
Jan 3 - Jan 4, 2026
Total with taxes and fees
Guests staying at Shadowcrest have access to a terrace, a garden, and a picnic area. You can take advantage of free parking if you drive. The 24-hour front desk has staff standing by to help with concierge services, and answer any questions about the accommodations. Additional amenities include a communal living room and barbecue grills.
Breakfast included
Pet friendly
The Old Catskill Game Farm Inn
400 Game Farm Rd Catskill NY
The Old Catskill Game Farm Inn features free WiFi in public areas, coffee in a common area, and a meeting room. If you decide to drive, there's free parking. Other amenities at this historic guesthouse include free newspapers, laundry facilities, and a communal living room.
Pet friendly
Parking included
Beds on Clouds
5320 Main Street Windham NY
$189 nightly
The price is $204 total per night
$204 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
Guests of Beds on Clouds enjoy free WiFi in public areas, express check-in, and express check-out. You can take advantage of free parking, along with an area shuttle for a fee. Front-desk staff can assist with tours/tickets and luggage storage. Additional amenities include a terrace, a picnic area, and a garden.
Parking included
Free WiFi
The Woodbine Inn
144 Malden Ave Palenville NY
At The Woodbine Inn, guests have access to free WiFi in public areas, express check-out, and laundry facilities. If you plan to drive, free parking is available. A multilingual staff is on hand to assist with luggage storage and tours/tickets. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Other amenities at this golf guesthouse include a garden, a picnic area, and barbecue grills.
Pet friendly
Parking included
Catskills Hideaway w/ Sauna Minutes from Hiking
Mount Tremper NY
Guests staying at this guesthouse have access to barbecue grills and a garden.
Pet friendly
Air conditioning
LEEDS A GREAT ESCAPE
Leeds NY
Guests staying at this guesthouse have access to barbecue grills and a garden.
Air conditioning
Parking available
Gateway Lodge Bed & Breakfast
11 Highlands Road Highmount NY
Guests of Gateway Lodge Bed & Breakfast enjoy free WiFi in public areas, meeting rooms, and a terrace. You can put free parking to good use if you drive. Staff members can help with accommodation requests, and provide front-desk service during limited hours. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a garden, a picnic area, and barbecue grills.
Pet friendly
Parking included
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 Windham
Hotel Vienna
107 State Route 296 Windham NY
$159 nightly
The price is $172 total per night from Jan 5 to Jan 6
$172 total
Jan 5 - Jan 6, 2026
Total with taxes and fees
9.2/10 Wonderful! (720 reviews)
Eastwind Windham
5088 NY-23 Windham NY
$249 nightly
The price is $268 total per night from Jan 6 to Jan 7
$268 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
9.2/10 Wonderful! (75 reviews)
Wylder Hotel Windham
19 New York 296 Windham NY
$315 nightly
The price is $341 total per night from Jan 6 to Jan 7
$341 total
Jan 6 - Jan 7, 2026
Total with taxes and fees
8.6/10 Excellent! (89 reviews)
Windham Guest Houses essential information
Accommodation | 9 Guest Houses |
|---|---|
Lowest Price | $162 |
Highest Price | $341 |
Popular accommodation | The Herwood Inn, Shadowcrest, The Old Catskill Game Farm Inn, Beds on Clouds, The Woodbine Inn, Catskills Hideaway w/ Sauna Minutes from Hiking, LEEDS A GREAT ESCAPE, Gateway Lodge Bed & Breakfast |