Windham County Holiday Rentals

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Our top choices for Windham County holiday rentals

Front of property

Marlboro Escape: 9 Mi to Mount Snow Resort!

Marlboro Escape: 9 Mi to Mount Snow Resort!
3.0 star property
Wilmington
Marlboro Escape: 9 Mi to Mount Snow Resort!
Outdoor spa tub

Long Trail House at Stratton Mountain Resort

Long Trail House at Stratton Mountain Resort
3.0 star property
Stratton
8.6 out of 10, Excellent, (83 reviews)
"Nice place and great location!!!"
United States
William
The price is HK$2,542
HK$3,160 total
includes taxes & fees
15 Apr - 16 Apr
Long Trail House at Stratton Mountain Resort
Exterior

Charming Fully Renovated One-Room Schoolhouse on 22+ acres

Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Grafton
9.6 out of 10, Exceptional, (168 reviews)
"Very nice and clean cabin, not too far from small towns, decently supplied for expected conveniences, charming area - a small stream nearby provides a pleasant background noise. "
United States
Philip
The price is HK$1,331
HK$2,719 total
includes taxes & fees
9 Apr - 10 Apr
Charming Fully Renovated One-Room Schoolhouse on 22+ acres
Fridge, microwave, oven, stovetop

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!

Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Dover
10.0 out of 10, Exceptional, (13 reviews)
"great location easy access to the mountain and the pool was outstanding."
United States
jim f.
The price is HK$3,630
HK$9,121 total
includes taxes & fees
6 Apr - 7 Apr
Brand New Listing! Amazing 4 Bedroom Townhome with your own private Hot Tub!!!
Living area

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham

Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Whitingham
8.8 out of 10, Excellent, (3 reviews)
"The was an excellent experience all around! The place is immaculate and exactly as described, stylish and functional for our group of 8. Appreciated the fireplace, flat screens and PacMan. Check in/out instructions clear and communication w owner quick. The location was convenient for skiing Mt Snow. Jax on Tap a great spot right below for dinner and fun- our crew played shuffleboard and pool. Food was delicious! "
United States
Claudia M.
The price is HK$2,851
HK$5,053 total
includes taxes & fees
30 Mar - 31 Mar
Stay in this historic Automotive-themed huge Apt. Located in charming Whitingham
Outdoor pool, a heated pool

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den

2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Dover
9.4 out of 10, Exceptional, (23 reviews)
"Perfect spot for Mount Snow "
United States
Bobby
The price is HK$480
HK$2,471 total
includes taxes & fees
31 Mar - 1 Apr
2BR 1BA - MT SNOW, SKI BACK TRAIL, FREE SHUTTLE, POOL, BBQ - Green Mountain Den
Exterior

Insanely romantic treehouse perched next to a stream and rolling hills.

Insanely romantic treehouse perched next to a stream and rolling hills.
Londonderry
10.0 out of 10, Exceptional, (2 reviews)
"Very nice secluded treehouse. We would definitely recommend!"
United States
Beth H.
The price is HK$3,102
HK$6,868 total
includes taxes & fees
30 Mar - 31 Mar
Insanely romantic treehouse perched next to a stream and rolling hills.
Property grounds

Lake Whitingham & Mount Snow Area Village Apartment

Lake Whitingham & Mount Snow Area Village Apartment
Whitingham
10.0 out of 10, Exceptional, (1 review)
"This place was cozy and romantic, making it the perfect escape from the hustle and bustle of city life. The location is ideal, with charming New England towns to explore in every direction. Amy and Connor were exceptional hosts, checking in with us throughout our stay to ensure we felt right at home."
United States
Anicia K.
The price is HK$1,097
HK$2,395 total
includes taxes & fees
1 Apr - 2 Apr
Lake Whitingham & Mount Snow Area Village Apartment
Fridge, microwave, stovetop, dishwasher

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake

Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Whitingham
10.0 out of 10, Exceptional, (2 reviews)
"as advertised."
United States
Joshua G.
The price is HK$3,791
HK$6,246 total
includes taxes & fees
2 Apr - 3 Apr
Amazing 34 foot high shipping container home in Whitingham on Sadawga Lake
Terrace/patio

Vikings Villages Resort - Double Bed Room

Vikings Villages Resort - Double Bed Room
Guilford
The price is HK$1,762
HK$2,193 total
includes taxes & fees
30 Mar - 31 Mar
Vikings Villages Resort - Double Bed Room
Interior

Family-friendly Stratton Gem Close to Slopes!

Family-friendly Stratton Gem Close to Slopes!
3.5 star property
Stratton
Family-friendly Stratton Gem Close to Slopes!
Smart TV, fireplace

Luxury Condo Stratton Mountain

Luxury Condo Stratton Mountain
Stratton
10.0 out of 10, Exceptional, (2 reviews)
"Katherine was a perfect host. The house is beautiful and had everything we needed for our family vacation. Thank you so much! "
United States
Katryn B.
The price is HK$16,135
HK$21,555 total
includes taxes & fees
1 Apr - 2 Apr
Luxury Condo Stratton Mountain
Fridge, oven, stovetop, dishwasher

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub

Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Londonderry
7.0 out of 10, Good, (2 reviews)
"I was "sold" & excited when I saw the pictures online bc the barn looked really neat. Although the barn was a neat concept, the pictures ARE NOT accurate, it is not as updated as pictured & it was VERY DISAPPOINTING. I now understand the non-refundable policy bc what you see online is definitely NOT what you walked into when you opened the door & they don't want to have to give people their back. Although we had fun, the accommodations were VERY misleading & disappointing. "
United States
Christine M.
The price is HK$1,988
HK$3,866 total
includes taxes & fees
30 Mar - 31 Mar
Enjoy this authentic and cozy VT Barn with Brand New Hot Tub
Smart TV, fireplace

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!

Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
Londonderry
10.0 out of 10, Exceptional, (10 reviews)
"Great location, well-designed house, and a beautiful view."
United States
Marcel P.
The price is HK$1,938
HK$4,952 total
includes taxes & fees
2 Apr - 3 Apr
Newly built Vermont secluded cabin retreat with AC and brand new Hot Tub!!!
Interior

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

Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Londonderry
8.2 out of 10, Very good, (11 reviews)
"We had a wonderful stay."
United States
Joshua
The price is HK$2,573
HK$4,421 total
includes taxes & fees
30 Mar - 31 Mar
Treehouse lifted up over a stocked trout pond up in the beautiful birch trees!
Exterior

Romantic Riverbed Treehouse - hot tub & new sauna!

Romantic Riverbed Treehouse - hot tub & new sauna!
londonderry
9.6 out of 10, Exceptional, (5 reviews)
"Great little space"
United States
John
The price is HK$1,473
HK$5,019 total
includes taxes & fees
1 Apr - 2 Apr
Romantic Riverbed Treehouse - hot tub & new sauna!
Interior

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Dover
9.8 out of 10, Exceptional, (15 reviews)
"We enjoyed our stay."
United States
Anonymous traveller
The price is HK$1,755
HK$4,391 total
includes taxes & fees
6 Apr - 7 Apr
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.
Property grounds

Family Friendly Hilltop House In Putney Vermont

Family Friendly Hilltop House In Putney Vermont
Putney
9.4 out of 10, Exceptional, (59 reviews)
"The host and her daughter were lovely and kind and very quick with all communication."
United States
Susan O.
The price is HK$1,300
HK$2,421 total
includes taxes & fees
30 Mar - 31 Mar
Family Friendly Hilltop House In Putney Vermont
Fridge, microwave, oven, stovetop

Stratton Mtn Studio | Renovated | Walk to Lifts

Stratton Mtn Studio | Renovated | Walk to Lifts
Stratton Mountain
10.0 out of 10, Exceptional, (31 reviews)
"Great location."
United States
Jeffrey
The price is HK$1,559
HK$3,390 total
includes taxes & fees
13 Apr - 14 Apr
Stratton Mtn Studio | Renovated | Walk to Lifts
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 County Hotel Reviews

Chalet 239

Chalet 239

8/10 Good
"Only issue is there was nowhere to hang anything and the room was very small. Room was clean, comfortable and bathroom was well-appointed. Breakfast was good and staff friendly and helpful. Close to restaurants and super easy access to Mt. Snow. Would definitely stay here again. "
Mary 1-night trip
Posted 21 hours ago
Chalet 239