
House vacation rentals in Windsor
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Top-rated house rentals in Windsor
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WeHa Penthouse w/ Private Deck
Welcome to our cozy penthouse-style apartment, where comfort meets tranquility. Enjoy a private deck with exceptional views of West Hartford. Treat yourself with our minibar and indulge without leaving your unit. Centrally located, our apartment provides easy access to the best of West Hartford. Explore Blue Back Square, a vibrant dining hub just 5 minutes away. For a leisurely experience, walk 2 minutes to Park Rd and discover culinary delights like Plan B, Americano Bar, and Zaytoon’s Bistro.

Luxury Stay in Expansive Historical Home
The Bassett House, originally built in 1802, this large historic farmhouse was elegantly remolded in 2018. North Haven, CT is centrally located and just minutes from Yale, Quinnipiac, UNH, and SCSU as well as shopping, the best restaurants, hiking trails state parks and beaches, and many local attractions including various vineyards. If you’re planning a business trip or a gathering for family or friends, then our home can provide you with an exceptional level of comfort during your time in CT!

Connecticut Chalet: Winter Nights by the Fire
Escape to a unique & stylish home perfectly tucked away in a picturesque New England town. Indulge in the privacy & serenity of this 5 acre wooded property and peaceful pond while being minutes from an abundance of restaurants, shops & entertainment. Enjoy the natural setting from the comfort of the glass enclosed sunroom with panoramic views of the property. This 3 bed, 2 bath home maintains it’s original 1960’s charm while boasting thoughtful modern touches and intentional functionality.

Modern ~ 3 Bedroom ~ Sleeps 8 ~11 mins to Hartford
Have fun with the family at this stylish and modern house! You will be welcomed with coziness. Kitchen is fully equipped. The bedrooms have queen beds and black out curtains. You will find a sofa bed and twin bed in the enclosed fancy porch making it possible to host 8 people. There is 1 full bathroom on lower lever and another full bathroom on the upper floor. House is equipped with an office desk and chair with WiFi suitable for a home office. Living room & Porch have a smart TV!

Cozy cottage 5 minutes from UConn
Wake up to the morning sun over the lake in the loft, or rise after the sun in one of the two back bedrooms. Enjoy a morning coffee or tea while enjoying the lake view from the bar top overlooking the water and watch for the Swans, Bald Eagles, and Blue Herons. After a hike on the trails, kayaking up the lake into conservation land, or fishing off the dock, relax in the hot tub. As the sun sets over the trees cuddle up on the couch with a good book and keep an ear out for the owls.

Cozy Family Home - Kid & Pet Friendly
3 bedroom house on a quiet street. 5mins down the road from ESPN and Lake Compounce. Kid friendly. Pet friendly. Workspace available. 1 bedroom w/ king bed. 1 bedroom w/ queen bed. 1 bedroom w/ 2 twin beds. Fully finished basement with 60inch TV, kids toys and fitness equipment/stationary bike. Deck and below deck hang out space. Though we aren’t living here full time, it’s still the place we call home, and we will use it when it’s not booked. Long stays welcome.

Farm Fresh Feeding Hills
Private in-law suite attached like a garage. Best view in the house overlooking the pond, ducks, goats, horses, & mtn. 1 Bedroom, small shower stall bath, combo kit/lvg room and a screened porch. Approx. 600 sq ft. ttl. The space is perfect for 2 people, ok for 4 and a squeeze for 6 people. Only a few miles to The Big E, 6 Flags, MGM Casino, BB Hall of Fame & Dr. Suess. 20 ish min to Hartford Int. Airport, 30 ish to Htfd & 40 ish north to 5 college area.

Best River View, on Rail Trail in Collinsville!
This quaint and spotless home is perched on a knoll across the road from the Farmington River & Rails to Trails you can walk to restaurants, gift shops & antique shops; Canoe/Kayak/Paddleboard; go fishing; enjoy the Farmington River Rail Trail; hiking trails, and Ski Sundown close by; or just relax & enjoy the view! Enjoy the best view in Collinsville - one of "America's 10 Coolest Small Towns" by Arthur Frommer's Budget Travel Magazine. Beautiful year round!

Litchfield County Farmhouse with a Modern Twist
Litchfield County farmhouse (c.1890) with a modern studio addition and distinctive interiors that feature a number of mid-century modern furnishings. The owners are a writer and an architect who have built a truly unique home full of original art and a large book collection. The property itself is small but it is surrounded by 250 acres of farmed conservation land and a short walk will take you past some of the most scenic farms in Litchfield County.

Modern Farmhouse
This is a quaint, sun-filled farmhouse in the Farmington valley of Connecticut. Convenient to great antique shopping, Ski Sundown, farm stands, Farmington river inner-tubing and biking trails, kayak and canoe rentals, the sweet towns of Collinsville and New Hartford, and a 30 minute straight shot to Hartford itself. The house is also convenient to Torrington, Simsbury, Avon, Winsted, and a beautiful drive to Hartford-Bradley International Airport.

Sunrise on the Water's Edge - Riverside Bungalow
Cozy riverside bungalow celebrates panorama views of the peaceful Connecticut River. Multiple levels of outdoor living space, open-air and screened-in. Just minutes from all major points of interest in the Pioneer Valley - including Six Flags New England, MGM Casino Complex, Big E Fairgrounds, Basketball Hall of Fame, and the Greater Springfield Metro area. Only 20 minutes from Bradley International Airport (BDL) in Windsor Locks.

Paradise On The Hill Luxury Apartment.
Enjoy your own special and separated section of this beautiful, modern colonial home. This beautiful home includes an oversize living room with a comfortable Queen Size sectional sleeper sofa, oversize Master Bedroom and very large bathroom with spa like jets. His and hers closets. Beautiful kitchenette. 50 inch T.V., Free WiFi. , comfortable dining and more, all for the comfort and convenience of our guests.
Popular amenities for Windsor house rentals
House rentals with a pool

Casino Wine Down House with Winter Igloo

Hilltop House w/POOL/SPA- HOST & Co.

Hot Tub~Pool~GameRoom~FirePit~BBQ~King Bed~Casinos

Sleeping Giant Stay/Swim Spa w/Tread/Tonal/Peleton

Stunning Views, Bucolic Bliss in 1790s Farmhouse

mid century ranch style house on farmland

Grand 9 BR Near Casinos

Beauty and the Beach!
Weekly house rentals

Charming Cape Home, Close to All

Renovated Single Family Home

By The River

The Hangar

Nest&Rest Escape

Heart of Hartford

The little house that could!

Great Home Office and Chef's Kitchen in Longmeadow
Private house rentals

Retreat Bolton Lake

Cozy Waterfront Home w/ Hot Tub Connecticut River

Renovated & Modern Victorian in Historic West End

Cozy Hall of Fame Gem

Private Woodland Sanctuary—3 mins to a lake beach!

The Walnut Apartment

Bright & Private WHOLE HOUSE 4 YOU Near Everything

Heart of Connecticut - New England (1800 sq ft)
When is the best time to visit Windsor?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ426 | ﺩ.ﺇ426 | ﺩ.ﺇ441 | ﺩ.ﺇ507 | ﺩ.ﺇ441 | ﺩ.ﺇ441 | ﺩ.ﺇ441 | ﺩ.ﺇ441 | ﺩ.ﺇ466 | ﺩ.ﺇ507 | ﺩ.ﺇ459 | ﺩ.ﺇ485 |
| Avg. temp | -3°C | -1°C | 3°C | 10°C | 16°C | 20°C | 24°C | 23°C | 18°C | 12°C | 6°C | 0°C |
Quick stats about house rentals in Windsor

Total vacation rentals
Explore 40 vacation rentals in Windsor

Nightly prices starting at
Windsor vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 840 verified reviews to help you choose

Family-friendly vacation rentals
20 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
40 of Windsor vacation rentals include wi-fi access

Popular amenities for guests
Guests love Kitchen, Wifi, and Pool across Windsor rentals

4.7 Average rating
Windsor stays receive an average rating of 4.7 out of 5 from guests
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- Yale University
- Foxwoods Resort Casino
- Six Flags New England
- Ocean Beach Park
- Catamount Mountain Ski Resort
- Bash Bish Falls State Park
- Butternut Ski Area and Tubing Center
- Kent Falls State Park
- Mohegan Sun
- Mohawk Mountain Ski Area
- Mount Southington Ski Area
- Taconic State Park
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Mystic Seaport Museum
- Norman Rockwell Museum
- Sleeping Giant State Park
- Yale University Art Gallery
- Berkshire Botanical Garden
- Ski Sundown
- Naumkeag
- Bluff Point State Park
- Connecticut Science Center
- Devil's Hopyard State Park




