Vacation Homes in Windsor, VT
Seize Your Someday with our amazing deals for the whole family!
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top Vacation Homes in Windsor

Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen

Okemo Mountain Lodging

Beautifully renovated with fireplace and coffee bar

Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table

Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking

Spacious 3BR Home Near Lake & Mountain - Sleeps 9 - Sunapee Retreat

Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated

MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!

Lakefront home with amazing views, fireplace, firepit, & gas grill
Top hotels in Windsor

Fat Sheep Farm & Cabins
Find the Best Vacation Homes in Windsor
Why book a vacation home in Windsor?
Vacation homes in Windsor make for a different travel experience. Your holiday home will allow you to feel at home during your visit. You’ll usually have more space, more privacy, and extra amenities not typically included with hotel stays.
How much is a vacation home in Windsor?
Private Windsor rental homes range between $121 - $428 per night. Prices change based on seasonal demand, travel dates, property location, capacity, amenities, etc.
What are the cancellation and flexibility options on Travelocity?
To cancel your vacation home, you must reach out to the individual property manager. Their contact details are available in your itinerary. For more information, head over to our customer service portal. Use the ‘free cancellation’ or ‘reserve now, pay later’ filters to find the most flexible options for your bookings.
What amenities should I look out for in a vacation home?
There are some exciting amenities available in Windsor vacation home rentals. You might look for Windsor rental houses with a private pool or free Wi-Fi. Some popular amenities also include a private hot tub, air-conditioning, laundry facilities, and a games room.
Vacation rentals in Windsor offer other accommodations that may interest you. Some have resort-like amenities such as a fitness center, bar/lounge, or swimming pool.
When is the best time to rent a vacation home in Windsor?
You’ll typically get cheaper rates when staying during the off-season, . Prices are usually at their lowest for stays in . are the most popular months to visit.
Why book a vacation home with Travelocity?
Travel smart with Travelocity. Search over 1 million properties worldwide and access an incredible selection of holiday homes in Windsor. Our members save 10% or more on select hotels, and if you find a lower price, we’ll match it with our Price Match Guarantee. Get started finding Windsor hotels and vacation homes that best suit your stay. We also have deals for flights, and Windsor car rentals. You’ll save even more when you bundle your items into a Windsor vacation package!
How many vacation homes are available to book in Windsor?
There are 763 rental homes in Windsor. Enter your travel dates to check availability.
How do I find the best price for a vacation home in Windsor?
Private vacation homes vary in price, and we’ll help you get the best deal possible. Use the map feature to compare rental house prices in different neighborhoods. Also, try adjusting your dates to compare nightly rates within a similar timeframe.
Windsor Vacation Homes essential information
Accommodation | 763 Vacation Homes |
---|---|
Lowest Price | $121 |
Highest Price | $428 |
Popular accommodation | Traveling with kids? Try this secluded & updated 3-bedroom home close to Okemo, Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable, Quiet Modern Luxury Home w/ Memory Foam Beds, A/C, FAST WiFi and Full Kitchen, Okemo Mountain Lodging, Beautifully renovated with fireplace and coffee bar, Classic VT Ski Chalet - Walkable to Okemo Ski Lift w/Fit Pit & Pool Table, Spacious Vermont Getaway 7 BR/4.5 BA - Close to Skiing - Biking - Golf - Hiking, Spacious 3BR Home Near Lake & Mountain - Sleeps 9 - Sunapee Retreat, Ski-On/Off - private sauna - right next to lift - 1GB WiFi - Renovated, MountainView - Luxurious 5800SF Retreat with Breathtaking 4-Season Views!, Lakefront home with amazing views, fireplace, firepit, & gas grill, Beautiful 4-bedroom House and Treehouse 5 min to skiing, hiking, golf, biking. |
More ways to wander Windsor
Explore More Ways to Travel with Travelocity
- Hotels near Quechee Gorge Bridge
- Farmstay in South Woodstock
- B&B in South Woodstock
- Pet Friendly Hotels in South Woodstock
- South Woodstock Hotels
- Resorts in South Woodstock
- Hotels near Green Mountain Rock Climbing Center
- B&B in Windsor Station
- Reading Hotels
- Resorts in Reading
- Hotels near Simon Pearce Mill
- Hotels near Quechee State Park
- B&B in Perkinsville
- Perkinsville Hotels
- Motels in Perkinsville
- Hotels near Mt Ascutney State Park
- 5 Star Hotels in Brownsville
- Apartments in Brownsville
- B&B in Brownsville
- Cabins in Brownsville
- Guest Houses in Brownsville
- Boutique Hotels in Brownsville
- Hotels with Bar in Brownsville
- Pet Friendly Hotels in Brownsville
- Spa Resorts & in Brownsville
- Brownsville Hotels
- Rv Parks in Brownsville
- Villas in Brownsville
- Hotels near Upper Valley Aquatic Center
- Casino Resorts & in Woodstock
- Kid Friendly Hotels in Woodstock
- Hotels with Balconies in Woodstock
- Hotels with Hot Tubs in Woodstock
- Hotels with an Indoor Pool in Woodstock
- Pet Friendly Hotels in Woodstock
- Romantic Getaways & Hotels in Woodstock
- Spa Resorts & in Woodstock
- Woodstock Hotels
- Hotels near VINS Nature Center
- 4 Star Hotels in Hartland
- B&B in Hartland
- Cabins in Hartland
- Chalets in Hartland
- Cottages in Hartland
- Hartland Hotels
- Resorts in Hartland
- B&B in Cavendish
- Cottages in Cavendish
- Ski Resorts and in Cavendish
- Spa Resorts & in Cavendish
- Cavendish Hotels
- 4 Star Hotels in Taftsville
- B&B in Taftsville
- Cottages in Taftsville
- B&B in Ascutney
- Condos in Ascutney
- Cheap Hotels in Ascutney
- Ascutney Hotels
- Inns in Ascutney
- Hotels near Mount Ascutney
- Hotels near Quechee Gorge Village
- Casino Resorts & in Quechee
- Cheap Hotels in Quechee
- Golf Resorts & in Quechee
- Hotels with an Indoor Pool in Quechee
- Luxury Hotels in Quechee
- Pet Friendly Hotels in Quechee
- Romantic Getaways & Hotels in Quechee
- Ski Resorts and in Quechee
- Spa Resorts & in Quechee
- Quechee Hotels
- Hotels near Route 4 Glassblowing Studio
- Hotels near Harpoon Brewery
- Farmstay in Weathersfield
- Cabins in Weathersfield
- Extended Stay Hotels in Weathersfield
- Weathersfield Hotels
- Inns in Weathersfield
- Motels in Weathersfield
- Hotels near Vermont Institiute of Natural Science