
Search Holiday Rentals in Windsor
- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Check prices for these dates
Our top choices for Windsor holiday rentals

1. Fat Sheep Farm & Cabins
Fat Sheep Farm & Cabins
2. Cabin on the hill Ascutney Vt - 4 bedrooms
Cabin on the hill Ascutney Vt - 4 bedrooms
3. Addie's Place: A Quiet and Quirky Guesthouse
Addie's Place: A Quiet and Quirky Guesthouse
4. Adventure Cabin Hot Tub Sauna Trails Game Area
Adventure Cabin Hot Tub Sauna Trails Game Area
5. Bridgewater Living - Ben&Jerry Suite
Bridgewater Living - Ben&Jerry Suite
6. Modern Village Condo Steps to Dining & Ski Shuttle
Modern Village Condo Steps to Dining & Ski Shuttle
7. Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails
Cozy Resort Cabin! Hot-Tub Sauna Fire Pit Trails
8. Lux Cabin Hot-Tub, Sauna, Private Fire Pit, Grill, Snow Shoes
Lux Cabin Hot-Tub, Sauna, Private Fire Pit, Grill, Snow Shoes
9. Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge
Ground-floor ski-in/ski-out condo facing the Clock Tower base lodge
10. Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts
Okemo ski-in/ski-out condo a few feet from the A and B Quad lifts
11. Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!
12. First-floor downtown studio near dining and gear shops, under a mile to Okemo
First-floor downtown studio near dining and gear shops, under a mile to Okemo
13. Bridgewater Living - Ski VT Suite
Bridgewater Living - Ski VT Suite
14. Downtown Ludlow condo with electric fireplace, shuttle stop across the street
Downtown Ludlow condo with electric fireplace, shuttle stop across the street
15. Lakefront Family Fun Retreat
Lakefront Family Fun Retreat
16. Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
Designer Cabin w/ Quechee Club Access - Pool, Spa, Ski - Sleeps 8
17. Compact downtown studio condo with kitchenette near the Okemo slopes
Compact downtown studio condo with kitchenette near the Okemo slopes
18. Mountain Green ground-floor condo with private yard off the patio
Mountain Green ground-floor condo with private yard off the patio
19. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington
20. Pet Friendly | Game Room | Minutes to Woodstock and Killington
Pet Friendly | Game Room | Minutes to Woodstock and KillingtonFind holiday rentals that suit your style
Top Windsor Hotel Reviews

Six South St Hotel
Find out more about Windsor
Everything you need to know about Windsor holiday rentals
Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Windsor holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!
There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Windsor holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Windsor holiday rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Windsor. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .
Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Windsor holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Windsor holiday rentals we have selected for you start as low as £132 per night. Entering your travel dates in the search wizard you might find even better deals!
How to find incredible deals on Windsor rentals
At Expedia, we put the best Windsor holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.
To find some top Windsor rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Windsor holiday.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Windsor. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.
Explore a world of travel with Expedia
- Genuine Farm!
- Harvest Barn Inn
- Rodeway Inn Bellows Falls
- Brookside Cabin + Hot Tub
- Bridgewater Corners Hotels
- Holiday Inn Club Vacations Mount Ascutney Resort by IHG
- Castle Hill Resort And Spa
- Gay-Friendly Hotels in Central Vermont
- Hotels with Connecting Rooms in Central Vermont
- Hotels with smoking rooms in Central Vermont
- Fat Sheep Farm & Cabins
- Inn at Water's Edge
- Log Cabin
- Cozy Vermont Cabin at Trail End Ranch! The Best of VT is all around you!
- Chester Hotels
- Grafton Inn
- Chalets in Killington
- Cottages in Killington
- 106 One bedroom Queen Suite on the 1st floor w/ outdoor heated pool
- Alpine Oasis Studio at Mountain Green Resort Killington
- Bearhaus Central AC
- Bearitime Lodge Pool
- Mightymoose
- Bigelow Chalet at Killington
- Private Post & Beam Home Ideal for Family or Group Gatherings
- Fall Line Condo E1 1 Bedroom Condo
- Gay-Friendly Hotels in Killington
- Luxury Hotels in Killington
- Newly Renovated Killington House
- Robin`S Nest
- Sunbear
- Sunrise
- Sunrise West Glade K7 ski on ski off with a wonderful community sports center.
- Winding Way Chalet
- Killington Hotels
- Cozy 2 BR Ski
- Echo Lake Inn
- Gorgeous Ski Chalet with Game Room & Hot Tub on Okemo Mt. under 1 mile to base!
- Hilton Hotels in Ludlow
- Hotels with Gym in Ludlow
- Hotels with Hot Tubs in Ludlow
- Season rental Okemo Ski Season
- Charming 2-bedroom house with WiFi, AC in serene Mount Holly
- Hilton Hotels in North Thetford
- Condo Rentals in Norwich
- Norwich Hotels
- Hotels near Pico Mountain at Killington Ski Resort
- Mountainside Home
- Vt Retreat on Highland Golf
- On Golf Course
- Golf Course
- Pet
- Align Inn Vermont
- Quechee Hotels
- Sharon Hotels
- Panoramic Mountain View
- The Weston
- Gay-Friendly Hotels in White River Junction
- Views
- Sauna
- White River Junction Hotels
- Windsor Mansion Inn
- Windsor Hotels
- Historic Charm
- The Jackson
- Views! Sauna Historic
- Woodstock Hotels
- Calvin Coolidge Homestead
- Dorsey Park
- Killington Golf Course
- Killington Resort
- Killington Holidays
- Visit Killington
- Ski Holiday Packages Killington
- Visit Ludlow
- Visit North Pomfret
- Pico Mountain at Killington Ski Resort
- Plymouth Holidays
- Visit Quechee
- Snowdon Triple Ski Lift
- Visit Strafford
- Visit Weston
- Visit White River Junction
- Woodstock Holidays
- Visit Woodstock


































































