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Compare 139 Cottages in Windham with updated reviews, rates, and availability.

Streamside Cottage Walking Distance to Town of Woodstock
10.0 out of 10, Exceptional, (199)
"Very clean, just as advertised. The stream behind the cottage is beautiful! Will stay there again if we get a chance to revisit the area. The host was extremely accommodating and available🙂"
The price is SAR 709
SAR 1,346 total
includes taxes & fees
17 Jum. II - 18 Jum. II
Streamside Cottage Walking Distance to Town of Woodstock
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
10.0 out of 10, Exceptional, (38)
"We spent the weekend and had a wonderful time. The property was conveniently located near the center of town while still being very quiet and private. The cottage is perfect for a couple’s weekend getaway. Great spot if you want to have a jumping off point to explore the area. Would definitely stay again."
Junebug Cottage: peace, love and privacy a short walk to Woodstock village green
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
9.2 out of 10, Wonderful, (32)
"This is a great place to stay. Really loved the fire pit by the creek for evening cocktails and conversation."
The price is SAR 675
SAR 1,050 total
includes taxes & fees
16 Jum. II - 17 Jum. II
Charming Woodstock Teahouse Cottage by the Sawkill Creek trout stream
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Charming Artist's Retreat
10.0 out of 10, Exceptional, (114)
"This is our second time staying at the cottage. What beautiful weather in such a beautiful setting. Incredible motorcycle ride through the mountains. Thank you Maureen. Robin & Bruce"
Charming Artist's Retreat
Charming Cottage in Private Lake Community (Pet-Friendly!)
9.6 out of 10, Exceptional, (14)
"Clean and comfortable. We had a great time visiting with friends and family at my daughters baby shower!"
Charming Cottage in Private Lake Community (Pet-Friendly!)
Country Cottage with beautiful views and easy access to Catskills activities.
The price is SAR 413
SAR 654 total
includes taxes & fees
7 Raj. - 8 Raj.
Country Cottage with beautiful views and easy access to Catskills activities.
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
10.0 out of 10, Exceptional, (72)
"Charming cottage situated in the woods, close to main road, but not so close as to be bothered by road noise. it was clean and well-stocked and would definitely stay there again."
ADORABLE CREEK COTTAGE Charming Original Details, Fireplace, Near Town, WiFi
Modern Cottage 1 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
9.8 out of 10, Exceptional, (7)
"Definitely enjoyed my stay at the Lorca. It was clean, neat and tidy and was close to Belleayre. Peakamoose restaurant served an amazing dinner apres ski. Available grill and firepit provided a perfect getaway long weekend for us."
Modern Cottage 1 (The Lorca, Catskills) - 10 min to Belleayre, 25 min to Windham
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
10.0 out of 10, Exceptional, (111)
"We always enjoy returning to Brook Cottage Too so much. I feel myself relaxing as soon as we pull in – there is just such a peaceful vibe. Sitting on the little private patio, gazing out towards Overlook Mountain, is a particular favorite. You're close enough to everything in the village (you can walk to all the shops and restaurants), yet it still feels private. We can't wait to return!"
TOP-RATED! Pristine style+romantic luxury+firepit+walk to town=Brook Cottage Too
Stream Come True! Ski, hike, spa, flow, relax...
10.0 out of 10, Exceptional, (3)
"Tranquil sounds of flowing water all day was very relaxing. Property was just as described. Thank you!"
Stream Come True! Ski, hike, spa, flow, relax...
Saugerties Cottage - relaxing home in nature, close to downtown, HITS & hikes
10.0 out of 10, Exceptional, (2)
"We liked having two bedrooms and the size of the kitchen. Very convenient location. One suggestion is to have a lamp in the living room so it is usable at night."
Saugerties Cottage - relaxing home in nature, close to downtown, HITS & hikes
Modern Country Cottage
10.0 out of 10, Exceptional, (2)
"We were looking for a quiet getaway and found it! The house is updated, immaculate and fully appointed. It is well laid out with very comfortable furniture. There is a deck with a forest and a pond in the backyard, and a short walk through the forest to a creek. Very peaceful, with things to do in the area."
Modern Country Cottage
The Cabin at Chichester in the Catskills Mountains
9.8 out of 10, Exceptional, (165)
"Very clean, good area"
The Cabin at Chichester in the Catskills Mountains
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
9.8 out of 10, Exceptional, (126)
"This is a lovely cottage that's perfectly situated between the town of Woodstock and the Overlook Mountain trail. Wonderful ambiance, great mattress, generously-appointed kitchen. Only caveat is that the ceilings are quite low in some spots — especially the kitchen entrance and the upstairs loft-style bedroom. Bumped my head a few times when I forgot to duck!"
NEW! Herb Cottage: Historic Artist's Cottage, Wood Stove, Walk to Town!
Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn
10.0 out of 10, Exceptional, (7)
"Amazing place! So cozy and comfortable. Close to so many trails. We dropped off the kids at Hunter Mountain to snowboard both days and went for 2 amazing hikes. Perfect bluebird days! Will definitely be back!"
Catskills Cottage w/ Deck, 7 Mi to Hunter Mtn
5 mins to Belleayre Ski! Relax in Hot tub and turn on massage jets! Pets free!
9.8 out of 10, Exceptional, (9)
"We’ve stayed here twice now and would absolutely stay again. It’s a perfect cabin for our skiing getaway! The hot tub is great after skiing all day and the house had everything we needed for our stay. I especially loved that there were plenty of beds, a full bath on each floor, and comfy throw blankets. Staying here is so easy with our dog as well and we love any place that welcomes our pets as willingly as the owners here do. The house is full of charm, nicely decorated, and I would recommend...
5 mins to Belleayre Ski! Relax in Hot tub and turn on massage jets! Pets free!
Private Home ~ All Yours ~ Newly Renovated ~ In town ~ fenced in yard ~ Quiet
9.8 out of 10, Exceptional, (103)
"Dave's home is a wonderful property located in the center of Woodstock. Comfortable, clean with a wonderful fenced in yard that our dog loves. We have stayed here numerous times and continue to enjoy the wonderful feel of this home away from home! Love the wood burning fireplace on chilly and cold evenings. Beautiful yard! Quiet and relaxing! Very comfortable spaces in the home. Dave always responds within a very short period of time and is always helpful. Love the upgrades! We will definetly...
Private Home ~ All Yours ~ Newly Renovated ~ In town ~ fenced in yard ~ Quiet
Rose Cottage
Rose Cottage
Cozy Catskills Cabin with Mountain Views
10.0 out of 10, Exceptional, (20)
"Well stocked. Clean and inviting!! Enjoyed our stay."
Cozy Catskills Cabin with Mountain Views
Catskill Cottage, Walk to Downtown & River Views
10.0 out of 10, Exceptional, (2)
"We were looking for a place to stay when visiting our son who lives in the Catskill area. The cottage was perfect. It was in a great location in town close to breweries, shops, and restaurants. It was beautifully furnished and very spacious. We definitely plan on staying there again when we visit our son."
The price is SAR 375
SAR 638 total
includes taxes & fees
11 Jum. II - 12 Jum. II
Catskill Cottage, Walk to Downtown & River Views
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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.

Other property types in Windham

Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
10.0 out of 10, Exceptional, (131)
"We had a great time at Greg’s property. The house is huge and easily accommodated the 25 guests we had. It is very conveniently located for those that like to take advantage of skiing between Hunter and Windham mountains. Greg was extremely responsive and very easy to work with anytime we had questions arise. I would definitely recommend to others and will most certainly keep this place in mind for future trips! Thanks again!"
The price is SAR 4,107
SAR 6,702 total
includes taxes & fees
10 Jum. II - 11 Jum. II
Dancing Horse Farm in Windham: Spectacular 9 Bedroom Home, 30 Acres, Near Hunter
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.
9.8 out of 10, Exceptional, (86)
"Stayed here with a group of friends, and loved it! We had terrible weather, but the house was the best place to be stuck inside. We made pizzas in the outdoor oven, and enjoyed the hot tub. Can't recommend enough! The property manager Alan was awesome."
SOLAR ECLIPSE SPECIAL. Tuscan Year Round Beauty / Pickle Ball.
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
GREAT FOR FAMILIES! 3 MINUTE WALK TO MAIN STREET & 1 MILE FROM WINDHAM SKI MT.
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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