Guest Houses in Windsor County

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Check prices for these dates

Next weekend
29 Aug - 31 Aug
In two weeks
5 Sept - 7 Sept
In one month
19 Sept - 21 Sept
In two months
17 Oct - 19 Oct

Top Cities in Windsor County

Ludlow featuring street scenes
Guest HousesGuest Houses

Ludlow

Ludlow

Featured Guest Houses in Windsor County

Our top choices for Windsor County guest houses

Inn at Clearwater Pond (Quechee)
Gazebo

Inn at Clearwater Pond (Quechee)

3.5 star property
9.6 out of 10, Exceptional, (47)
"I booked two nights stay at this small, quaint, and very comfortable B&B in Quechee, VT. Tina, the owner, was a gracious, helpful host. The grounds around the property are tranquil and pristine. I would definitely stay there again."
Inn at Clearwater Pond (Quechee)
The Weston
Front of property

The Weston

5.0 star property
10.0 out of 10, Exceptional, (8)
"Incredible service. Staff was so attentive and knowledgeable. Room was great and the food was even better. A charming stay "
The price is HK$2,912
HK$3,175 total
includes taxes & fees
3 Sept - 4 Sept
The Weston
Mountain cabin by skiing with fireplaces & well-equipped kitchen - dog-friendly
Outdoor dining

Mountain cabin by skiing with fireplaces & well-equipped kitchen - dog-friendly

9.6 out of 10, Exceptional, (8)
"Property was perfect for a weekend trip to nearby Okemo (20mins). Would stay here again."
Mountain cabin by skiing with fireplaces & well-equipped kitchen - dog-friendly
Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts
Internet, bed sheets

Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts

9.4 out of 10, Exceptional, (35)
"Nice location,,, convenient to local attractions"
Perfect Vermont guesthouse getaway with mountain views & firepit - walk to lifts
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!
Exterior

1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!

9.4 out of 10, Exceptional, (39)
"We had a great time on our family ski trip."
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!
Ludlow Village Guest House - prime location on ski shuttle, walk to restaurants
Fridge, microwave, oven, stovetop

Ludlow Village Guest House - prime location on ski shuttle, walk to restaurants

9.8 out of 10, Exceptional, (42)
"Perfect location and very clean!"
Ludlow Village Guest House - prime location on ski shuttle, walk to restaurants
Salt Ash Inn
Billiards

Salt Ash Inn

3.0 star property
6.0 out of 10, (126)
Salt Ash Inn
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 Windsor County Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"This is a hidden gem. Probably my top 3 hotels I’ve ever visited. Classic, eclectic, vintage with modern convenience. The breakfast was perfect, staff included. Pool, sauna, drink bar and even the shampoo and shower gel are among the top in my list. We walked down to the river where my kids explored for 2 hours. I love this place. "
Aimee 1-night trip
Posted 2 days ago
On The River Inn