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Romantic Hotels in Windham County from $184

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Top Cities in Windham County

We were pretty impressed with this. Never seen a frozen body of water strong enough for all of this activity!
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Brattleboro

Brattleboro

Check availability on Windham County Romantic Hotels

Our top choices for Windham County romantic hotels

Reception
Grafton Inn

Grafton Inn

3.5 star property
Grafton
9.6 out of 10, Exceptional, (80)
"Wonderful in every way."
United States
Deborah
Grafton Inn
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers
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, (77)
"Nice, clean room in prime location"
United States
Kristin
$417 nightly
The price is $472
Dec 11 - Dec 12
Total with taxes and fees
Long Trail House at Stratton Mountain Resort
TV, fireplace
Mount Snow Condominiums

Mount Snow Condominiums

3.5 star property
West Dover
7.6 out of 10, Good, (81)
"We were very disappointed,the check in went smooth,but the condo itself was very disappointing.The minute we walked in the building it smelled terrible.Had no clue it was a basement condo or never would of booked it. The linen and couch itself smelled moldy and musty..there was a huge rip in the slider screen.Being a very hot and muggy night the mosquitoes were terrible.We checked out the next day and had to find another place to stay. Being from Massachusetts,we had no clue where to go.We...
United States
John
Mount Snow Condominiums
Indoor pool, a heated pool
Seasons On Mount Snow - Ski-in/Ski-out

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

Dover
9.8 out of 10, Exceptional, (180)
"Nice place to stay "
United States
Dean W.
Seasons On Mount Snow - Ski-in/Ski-out
Exterior
Stratton, Okemo, Bromley, Viking Nordic XC, Skiing!!

Stratton, Okemo, Bromley, Viking Nordic XC, Skiing!!

Londonderry
10.0 out of 10, Exceptional, (57)
"This is a fantastic house and perfect for a big group! We had 4 families and kids and everyone had a bed and plenty of space. Would highly recommend this house - especially for a ski trip to either Bromley or Stratton! "
United States
Kerry J.
Stratton, Okemo, Bromley, Viking Nordic XC, Skiing!!
Outdoor dining
Vantage Point Villas at Stratton Mountain Resort

Vantage Point Villas at Stratton Mountain Resort

3.0 star property
Stratton
8.4 out of 10, Very Good, (70)
"Amazing stay - The condo was cozy and perfect for our family! "
United States
Kate
$312 nightly
The price is $352
Dec 10 - Dec 11
Total with taxes and fees
Vantage Point Villas at Stratton Mountain Resort
TV
The Nutmeg

The Nutmeg

3.5 star property
Wilmington
9.4 out of 10, Exceptional, (414)
"This was a beautiful quaint property with delightful and attentive staff. The French toast breakfast was amazing! "
United States
John
$174 nightly
The price is $192
Jan 6 - Jan 7, 2026
Total with taxes and fees
The Nutmeg
Interior detail
The White House Inn

The White House Inn

3.5 star property
Wilmington
9.2 out of 10, Wonderful, (260)
"The room was beautiful and the historic charm was wonderful "
United States
Karin
$184 nightly
The price is $202
Jan 4 - Jan 5, 2026
Total with taxes and fees
The White House Inn
Porch
The Wilmington Inn

The Wilmington Inn

3.5 star property
Wilmington
10.0 out of 10, Exceptional, (195)
"Relaxing stay with great hiking nearby"
United States
Charlotte
$167 nightly
The price is $184
Dec 13 - Dec 14
Total with taxes and fees
The Wilmington Inn
Free WiFi, bed sheets
The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

3.0 star property
Stratton
7.6 out of 10, Good, (939)
"We like that getting to Stratton Mountain and the downtown area was very walkable or easy to get there by regularly running shuttle buses."
United States
Mark
$196 nightly
The price is $216
Jan 7 - Jan 8, 2026
Total with taxes and fees
The Black Bear Lodge at Stratton Mountain Resort
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

The Black Bear Lodge at Stratton Mountain Resort

The Black Bear Lodge at Stratton Mountain Resort

10/10 Excellent
"The staff are amazing! So friendly and welcoming. The lodge is so cute! The rooms were spotless and the hottub sparkling clean. The shuttle service until 10 pm was fantastic and the shuttle driver was very nice. We can't wait to visit again! "
Barbara 1-night trip
Posted 4 days ago
The Black Bear Lodge at Stratton Mountain Resort

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