Holiday Rentals in Windham County

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Top Cities in Windham County

Featured Holiday Rentals in Windham County

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very good, (72)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is €456
includes taxes & fees
30 Mar - 31 Mar
Long Trail House at Stratton Mountain Resort

Lovely ski-in/out condo steps from ski lift with trails and amazing views

8.8 out of 10, Excellent, (22)
"Unit is very close to ski lift. Ski in / ski out was great!!!"
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

10.0 out of 10, Exceptional, (45)
"Clean, ideal location, great communication."
The price is €348
includes taxes & fees
24 Mar - 25 Mar
Fantastic Townhouse on Mount Snow Shuttle – Prime Location for Your Adventure!

Stratton 1 Bedroom Long Trail Condo, Walk to Village and Lifts

9.6 out of 10, Exceptional, (50)
"We had a wonderful stay. The condo has everything you need, access to pool, hot tub and sauna and the location for skiing and spending time in the village is fantastic. Steve & Liz are clear, communicative and responsive hosts. "
Stratton 1 Bedroom Long Trail Condo, Walk to Village and Lifts

Updated Ski in ski out condo & mountain biking located at Seasons on Mt. Snow

10.0 out of 10, Exceptional, (52)
"The unit is great for a couple or small family and is stocked with just about anything you will need. It is conveniently located with a very short walk across the parking lot to the ski trail and also has a ski locker at the building entrance. The owners were super responsive to my questions and check-in/out was very easy. I highly recommend this property and would stay here again."
Updated Ski in ski out condo & mountain biking located at Seasons on Mt. Snow

MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain Den

9.4 out of 10, Exceptional, (13)
"Would have given 5-stars but the location is right below another rental and you can hear everyone walking around, which was a little annoying. After a friendly visit to the upstairs neighbors, and a cordial chat, it was a great evening. If the upstairs came with padded carpet this place would be a home run."
The price is €238
includes taxes & fees
3 Mar - 4 Mar
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain Den

SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

8.8 out of 10, Excellent, (42)
"We had a group of thirty-four people for a family vacation and had a blast. The host and the housekeeper were tremendously responsive to any small issues we had over the first few days. The kitchen was well stocked but could use more mugs for coffee/tea and additional forks for larger groups and the tea bags were past the best before date and should be replaced. Twelve bedrooms, each with their own bathroom was great. The pool, hot tubs, ping pong table, pool table, tennis court, and fire pit...
SLEEPS 32+ Indoor-pool, spa, sauna, fire pit & more! At the foot of MOUNT SNOW!

Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

7.0 out of 10, Good, (14)
"Great place. Clean and comfortable. Nicely stocked kitchen with newer appliances. Sauna was amazing. Had 10 inches of snow one morning and it was fully plowed by 7am!"
Stunning dog-friendly home with board games, sauna, balcony, gas grill, & deck

Stratton Mtn Studio | Renovated | Walk to Lifts

10.0 out of 10, Exceptional, (27)
"Nicely renovated, well equipped condo very conveniently close to the main lodge and all it offers. It is small but for two people it certainly is fine and murphy bed is a clever solution. Well done!"
The price is €601
includes taxes & fees
19 Mar - 20 Mar
Stratton Mtn Studio | Renovated | Walk to Lifts

Cabin 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK

2.0 star property
10.0 out of 10, Exceptional, (1)
"Cabin was as advertised and very close to the mountain. Would definitely stay again "
Cabin 7min to Ski Stratton-Wood Stove,Starry Skies,Fire Pit,Views,Dogs OK

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

8.6 out of 10, Excellent, (24)
"The apartment was in a great location to get to the ski lifts. "
The price is €322
includes taxes & fees
13 Mar - 14 Mar
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

9.8 out of 10, Exceptional, (114)
"Beautiful and peaceful, great house for a winter getaway with the family. We loved the yard and location. Grab your groceries on the way up, and enjoy the amazing house with your crew, (And dog too) "
This is it! Fabulous Vermont Cabin w/ 25 Acres to Explore! Spectacular Views!

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

9.6 out of 10, Exceptional, (154)
"Two friends and I stayed at this house for the second year in a row. It has been a perfect place for us, being 10 minutes away from Grafton and 25 minutes from Okemo."
The price is €360
includes taxes & fees
10 Mar - 11 Mar
Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

10.0 out of 10, Exceptional, (51)
"This place was just about perfect with excellent hosts that were easy to communicate to. My only ask would be to get shades to block the sun in the morning in the bedroom to the left of the upstairs bathroom. We did not use that bedroom because of this reason. That being said, we loved this place so much that we already booked again for next year. "
Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

10.0 out of 10, Exceptional, (46)
"We had a great stay at this property and every year a few families get together to spend a few days skiing and other winter activities. The house was a great layout for our group with plenty of spaces for all to sleep. Kids loved the downstairs while the adults love the game house. The property was well stocked with all needs if you forgot anything to make meal times easy. Host was great and if we had any questions they were answered right away. "
Escape in Rural Vermont! 2 Homes SaunaPool, Hot Tub, Game House Mountain Views.

MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain House

10.0 out of 10, Exceptional, (13)
"Six of us women from Vermont golf courses stayed while playing a tournament at Haystack Country Club. The house suited us perfectly. We had some issues with the bathtub plumbing not turning off but we had prompt attention from a service person. The house had a great kitchen and tv to accommodate us."
The price is €359
includes taxes & fees
19 Mar - 20 Mar
MT SNOW | SKI BACK TRAIL | FREE SHUTTLE - Green Mountain House

Stratton Mountain Resort Solstice Luxury 5 bedroom Ski-In/Out Vacation Home

9.8 out of 10, Exceptional, (50)
"Great location, ski in ski out, enjoyed the hot tub in the snow. Great for our group of 3 couples with young kids. Appreciated the well stocked kitchen. "
Stratton Mountain Resort Solstice Luxury 5 bedroom Ski-In/Out Vacation Home

**Stratton's Best Kept Secret** Ski On/Off ** Unit E

10.0 out of 10, Exceptional, (53)
"Great location for a ski vacation at Stratton. Just a 1 minute walk to the Tamarack lift. The townhouse was very clean and stocked with extra amenities. Perfect for a family of 4. The hosts were very responsive and helpful. "
**Stratton's Best Kept Secret** Ski On/Off ** Unit E

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

10.0 out of 10, Exceptional, (2)
"My husband and I stayed at the treehouse cabin for two nights. It was so adorable and had so many fun amenities from the hot tub, to the fire place and record player. They even had snow shoes for us to borrow and we were able to use them and had a fun morning snow shoeing. Easy check in, and just a nice clean fun place to stay."
The price is €610
includes taxes & fees
11 Mar - 12 Mar
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!

Seasons On Mount Snow - Ski-in/Ski-out

9.8 out of 10, Exceptional, (162)
"Great location and property. Owner communication was great. Overall the property was nice. An occasional deep cleaning is needed as the cleaning service really isn't doing a great job.Ski on/ off is great with kids as long as they are decent skiers. Could be challenging if someone was a newer skier."
The price is €279
includes taxes & fees
25 Mar - 26 Mar
Seasons On Mount Snow - Ski-in/Ski-out
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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