
Windsor Holiday Rentals
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Our top choices for Windsor holiday rentals

1. Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
Lakeside Escape - 4BR/2BA Retreat 2hrs from Boston
2. HotTub FirePit Games Huge Backyard Family Friendly
HotTub FirePit Games Huge Backyard Family Friendly
3. Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
Rustic & Renovated Hot Tub/Game Room Sleeps 8ppl
4. 16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
16+ppl 2 HotTubs Gamerooms FirePit 2 acre backyard
5. Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee
Tiffany Hill Treehouse by Sunapee Stays | Fireplace + Deck + Mount Sunapee
6. SUNAPEE RETREAT AT ENCHANTED FOREST - BRING KIDS - NEAR LAKE AND MOUNTAIN!
SUNAPEE RETREAT AT ENCHANTED FOREST - BRING KIDS - NEAR LAKE AND MOUNTAIN!
7. Brook Road Cabin
Brook Road Cabin
8. Family Friendly, Hot Tub, King Beds Just Renovated
Family Friendly, Hot Tub, King Beds Just Renovated
9. Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking
Peaceful Family Friendly Private Lake Waterfront Home Close to Skiing and Hiking
10. Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
Soonipi Casa by Sunapee Stays Peekaboo views of Mount Sunapee
11. Brook Road Cabin
Brook Road Cabin
12. Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
Hideaway By The Bay - 20ft boat slip and 4 minutes to Mount Sunapee
13. @SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
@SunapeeSeasons—Across from Dewey Beach, Lake View, 8 Min. from Mt. Sunapee
14. Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
Studio Apt with Full Kitchen. 1 minute stroll over picturesque bridge into town.
15. Cozy Tiny House on Main Street. Fully Renovated.
Cozy Tiny House on Main Street. Fully Renovated.
16. Room 10 - Queen Room
Room 10 - Queen Room
17. Brook Road Condo
Brook Road Condo
18. Lakefront Family Fun Retreat
Lakefront Family Fun Retreat
19. "Big Sky" Retreat Atop Sunapee / Ski + Lake Life
"Big Sky" Retreat Atop Sunapee / Ski + Lake Life
20. Cobb Meadow House: Cozy 5 Bedroom Retreat
Cobb Meadow House: Cozy 5 Bedroom RetreatFind holiday rentals that suit your style
Top Windsor Hotel Reviews

Courtyard by Marriott Keene Downtown
Find out more about Windsor
You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Windsor holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.
As much as you love your vacation rental, it’s always good to get out and explore to soak up Windsor. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Windsor. Seeing all the best attractions is bound to make you fall in love with Windsor. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Windsor short-term rentals, that won’t be hard to do.
































































