Holiday Homes in Windsor
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Windsor holiday homes
1. Beautiful 3-bedroom house with AC in charming Bridgewater
Beautiful 3-bedroom house with AC in charming BridgewaterBridgewater
10.0 out of 10, Exceptional, (1 review)
"Great house with fun decorations. Comfortable with lots of room; full kitchen with ample dining area. Loved the coffee available and the sound machine in the bedroom- great conveniences! Communication around booking were great with easy check in and check out."
Susan S.
The price is AU$777
includes taxes & fees
25 Aug - 26 Aug
2. Lakefront Family Fun Retreat
Lakefront Family Fun RetreatNewport
10.0 out of 10, Exceptional, (5 reviews)
"Great visit! The house is perfectly outfitted for a relaxing vacation. Super clean and updated. Really enjoyed the warm waters of Crescent Lake!"
Ann R.
The price is AU$592
includes taxes & fees
1 Sept - 2 Sept
3. Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson Gore
Charming Family Ski Chalet Less Than 5 minutes Drive to Okemo/Jackson GoreMt Holly
9.8 out of 10, Exceptional, (42 reviews)
"This house has great hang out space and plenty of space for a big family!"
Cheri V.
The price is AU$699
includes taxes & fees
19 Aug - 20 Aug
4. Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.
Cozy Vermont House Near Killington and Woodstock. Mountainside. Close to Slopes.Bridgewater
8.8 out of 10, Excellent, (3 reviews)
"Great place for a ski weekend"
Kathryn F.
The price is AU$997
includes taxes & fees
19 Aug - 20 Aug
5. Modern Farm House…minutes to Okemo; 2 King beds!
Modern Farm House…minutes to Okemo; 2 King beds!Mount Holly
9.6 out of 10, Exceptional, (19 reviews)
"Fantastic house! Christine was easy to communicate with and made us and our dogs feel incredibly welcome. Looking forward to staying there again."
Rachel L.
The price is AU$687
includes taxes & fees
19 Aug - 20 Aug
6. Okemo's Back Room - in the heart of the village on the shuttle route!
Okemo's Back Room - in the heart of the village on the shuttle route!Ludlow
9.6 out of 10, Exceptional, (16 reviews)
"Cool building, right on main street. Building is undergoing renovation on back porches so some construction material and disruption. The kitchen was not well equiped and needs an update. However, the space is really cool, very open, big bedrooms, decent bedding. Shower is a little small but nice. Good value"
jonathan w.
The price is AU$553
includes taxes & fees
20 Aug - 21 Aug
7. Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
Soonipi Casa by Sunapee Stays Peekaboo views of Mount SunapeeSunapee
10.0 out of 10, Exceptional, (58 reviews)
"Wonderful place to stay for our trip. Great location and the house was nicely updated. "
Andrew W.
The price is AU$606
includes taxes & fees
15 Sept - 16 Sept
8. @SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. SunapeeSunapee
10.0 out of 10, Exceptional, (26 reviews)
"The perfect winter stay for our family! Perfect location, close to Mount Sunapee. Gorgeous views and home. Host was extremely welcoming and responsive, and the whole stay was easy."
Amanda R.
The price is AU$733
includes taxes & fees
1 Sept - 2 Sept
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.
Find holiday rentals that suit your style
Cottages
Aparthotels
Save an average of 15% on thousands of hotels when you're signed in
Top Windsor Hotel Reviews
Fireside Inn & Suites West Lebanon
10/10 Excellent
Find out more about Windsor
Windsor Holiday Homes information
Number of reviews | |
|---|---|
Accommodation | Holiday Homes |
Lowest Price | |
Highest Price |