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. NEW RENO - Chalet-style farm loft near Tanglewood
NEW RENO - Chalet-style farm loft near TanglewoodNew Lebanon
8.6 out of 10, Excellent, (7 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
Joanna P.
The price is €205
includes taxes & fees
16 Aug - 17 Aug
2. Cozy Home in Pownal VT
Cozy Home in Pownal VTPownal
10.0 out of 10, Exceptional, (6 reviews)
"This home is super cozy and had all the amenities I needed after a long drive. I will be staying here again."
Jess M.
The price is €182
includes taxes & fees
16 Aug - 17 Aug
3. Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISOHancock
8.4 out of 10, Very good, (10 reviews)
"The owner was responsive. The heater worked well. The living spaces are as advertised. Traveling with 5 adults and a toddler; the layout is great. Convenient location for day trips and hiking."
Maura L.
The price is €533
includes taxes & fees
10 Sept - 11 Sept
4. Riverbend Berkshire East Basecamp - 3 bedrooms available
Riverbend Berkshire East Basecamp - 3 bedrooms availableCharlemont
10.0 out of 10, Exceptional, (5 reviews)
"Very nice house and the stay was unproblematic!"
Noah K.
The price is €411
includes taxes & fees
28 Aug - 29 Aug
5. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!Pittsfield
8.4 out of 10, Very good, (10 reviews)
"The space was well situated to our plans, food,lake and hiking and very clean but smelled sooo strongly of dogs that we limited our time inside."
Liz V.
The price is €518
includes taxes & fees
6 Sept - 7 Sept
6. Private bed with En-suite bathroom Marigold Room
Private bed with En-suite bathroom Marigold RoomShelburne Falls
The price is €189
includes taxes & fees
31 Aug - 1 Sept
7. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!Sherwood Forest
10.0 out of 10, Exceptional, (6 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
The price is €356
includes taxes & fees
9 Sept - 10 Sept
8. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
The price is €308
includes taxes & fees
9 Sept - 10 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
Aparthotels
Apartments
Save an average of 15% on thousands of hotels when you're signed in
Top Windsor Hotel Reviews
Vacation Village in the Berkshires
8/10 Good
Find out more about Windsor
Windsor Holiday Homes information
Number of reviews | 7,775 |
|---|---|
Accommodation | 267 Holiday Homes |
Lowest Price | €60 |
Highest Price | €232 |