Windsor Vacation Rentals
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 vacation homes
1. 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)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
Stephen L.
The price is CA $378
CA $699 total
includes taxes & fees
Oct 27 - Oct 28
2. Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISOHancock
8.8 out of 10, Excellent, (12 reviews)
"Host was proactive in communication and answer each and every question."
Amit
The price is CA $226
CA $768 total
includes taxes & fees
Oct 23 - Oct 24
3. Private bed with En-suite bathroom Marigold Room
Private bed with En-suite bathroom Marigold RoomShelburne Falls
The price is CA $162
CA $295 total
includes taxes & fees
Nov 8 - Nov 9
4. 5BR Berkshire Home Mins To The Mountain
5BR Berkshire Home Mins To The MountainCharlemont
10.0 out of 10, Exceptional, (8 reviews)
"What an amazing house to stay at! Tons of room, well equipped kitchen and a great location! "
Jason F.
The price is CA $457
CA $1,032 total
includes taxes & fees
Oct 25 - Oct 26
5. A roomy remodeled retreat close to MassMoCA
A roomy remodeled retreat close to MassMoCANorth Adams
10.0 out of 10, Exceptional, (61 reviews)
"Cute and comfy home. We enjoyed the unique decor and lack of TVs everywhere. It was a great break from all the crazy. Lots of conversation and togetherness."
Diane
The price is CA $322
CA $682 total
includes taxes & fees
Nov 1 - Nov 2
6. Greylock Cabin
Greylock CabinFlorida
10.0 out of 10, Exceptional, (7 reviews)
"This is a beautiful cabin on an amazing property with a great view of Mt Greylock! Clean, comfortable, great location, communication with the owner was outstanding and questions were answered quickly. It all went smoothly and we highly recommend this property!"
Margaret M.
The price is CA $392
CA $650 total
includes taxes & fees
Nov 17 - Nov 18
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, (10 reviews)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
Sharon K.
The price is CA $205
CA $526 total
includes taxes & fees
Oct 29 - Oct 30
8. Cozy Home in Pownal VT
Cozy Home in Pownal VTPownal
10.0 out of 10, Exceptional, (12 reviews)
"Absolutely wonderful place to stay. Quiet, clean, comfortable and close to a lot of things while feeling secluded. Owner communicated quickly and entry was easy. Loved every minute of our stay."
Jeri R.
The price is CA $163
CA $288 total
includes taxes & fees
Oct 26 - Oct 27
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 vacation rentals that suit your style
Apartments
Aparthotels
Save an average of 15% on thousands of hotels when you're signed in
Top Windsor Hotel Reviews
Hotel On North
10/10 Excellent
Find out more about Windsor
Windsor Vacation Homes information
Number of reviews | 239 |
|---|---|
Accommodation | 283 Vacation Homes |
Lowest Price | CA $288 |
Highest Price | CA $1,616 |
Explore a world of travel with Expedia
- Hotels near Berkshire East Ski Resort
- Pet-Friendly Hotels in North Adams
- The Red Door B&B
- Hotels with a Pool in Western Massachusetts
- Historic 1804 house in N Becket Village in the Berkshires
- Cottages in Mill River
- Plainfield Hotels
- Hotels with Kitchenettes in Western Massachusetts
- Condo Rentals in Otis
- Hotel Downstreet
- Hotels with Hot Tubs in Western Massachusetts
- Cheap Hotels in Lenox
- B&B in North Adams
- Motels in North Adams
- Hotels near The Clark Art Institute
- Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak
- Resorts in Lenox
- Condo Rentals in Florida
- Aparthotels in Williamstown
- Lee Hotels
- One Bedroom Luxury Cottage at Blantyre
- Guest Houses in Gill
- Lenox Hotels
- Villas in Beartown State Forest
- Lanesborough Hotels
- Chalets in Monroe
- Resorts in The Berkshires
- Apartments in Cheshire
- Washington Hotels
- Motels in Granville
- Cabin Rentals in South Amherst
- Hotels near Tanglewood Music Center
- B&B in Haydenville
- Chalets in Becket
- Hotels with an Indoor Pool in Western Massachusetts
- Hotels near Lee Premium Outlets
- 3 Star Hotels in Pittsfield
- Luxury Hotels in Berkshire County
- B&B in Lee
- B&B in Hadley
- Pet-Friendly Hotels in Western Massachusetts
- Oceanfront Hotels in Western Massachusetts
- North Adams Hotels
- Becket Hotels
- The Whitlock
- Pittsfield Hotels
- Chalets in Western Massachusetts
- Motels in Greenfield
- Pet-Friendly Hotels in Pittsfield
- Hotels with a Lazy River in Western Massachusetts
- Williamstown Hotels
- Hancock Hotels
- Lgbt Friendly Hotels in Cheshire
- Drury Hotels
- B&B in Florida
- Holiday Inn Express & Suites Pittsfield
- Cabin Rentals in Amherst
- Ashfield Hotels
- Motels in Shelburne
- Apartments in Huntington
- B&B in Adams
- Rv Parks in Leyden
- Charlemont Hotels
- Country Houses in Alford
- Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
- Cabin Rentals in Savoy
- Cottages in The Berkshires
- B&B in Russell
- Flights from Ithaca (ITH) to Pittsfield (PSF)
- Flights from Windsor
- Flights from Plattsburgh (PBG) to Pittsfield (PSF)
- Flights from North Adams
- Flights from Seattle (SEA) to Pittsfield (PSF)
- Flights to Williamstown
- Flights to Lenox
- Flights from Toronto (YYZ) to Pittsfield (PSF)
- Flights to Pittsfield
- Flights from Lenox
- Flights from Boston (BOS) to Pittsfield (PSF)
- Flights from Dalton
- Flights from Becket
- Flights to North Adams
- Flights to Western Massachusetts
- Flights from Phoenix (PHX) to Pittsfield (PSF)