
House vacation rentals in Windsor
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Top-rated house rentals in Windsor
Guests agree: these houses are highly rated for location, cleanliness, and more.

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.

Romantic Getaway at The Lake!
Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

Gardner Lake 2 Queen/1King/2 Bath/Laundry- Private
Stay with us for a relaxing, family lake vacation! Bring your family to our peaceful, private and BRAND NEW 3 bedroom - 2-bathroom home. We are located one block from the Gardner Lake public boat launch, easy access to the public beach. Just a short drive to Mystic, Stonington, Vineyards, Mohegan Sun & Foxwoods. Close to CT College, Mitchell, and USCGA. Cook your favorite meal in our fully equipped kitchen, you will think you never left home! Contact Peter or Adam to discuss your situation.

Luxe Bolton Lake
Lakefront jacuzzi for fall! Relax and enjoy the stylish comfort of our 3 bedroom/3 bathroom architecturally-designed lake home. The Luxe lake house features an expansive waterfront, outdoor jacuzzi, gorgeous primary bedroom suite w/ private shower and tub, artistic furniture, cozy fireplace, coffee bar, complimentary snacks, fast WiFi, large deck, fire pit, kayaks, vintage aluminum canoe, board games, and much more. Come stay at the Luxe lake house and make memories that will last a lifetime!

Connecticut Chalet: Experience Fall in New England
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.

Cozy Comforts!
Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

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!

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.

Charming home in West Hartford
Step into comfort in this beautifully updated second-floor apartment, complete with a fully equipped kitchen, a modern full bathroom, and two lovely queen-size bedroom designed for restful nights. Enjoy your morning coffee or evening wine on the private balcony, a perfect spot to unwind. Located just steps from iconic local favorites like the legendary Park Lane Pizza, you'll be at the center of West Hartford’s vibrant dining scene.

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

Waterview Cove 1 @ Ocean Beach: 6 Queen 1 Sofa Bed

Cedar Ridge: House

Mountaintop Nirvana: Lake, Pool, Hot Tub, Nature

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

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

Casino Stay & Play House

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Grand 9 BR Near Casinos
Weekly house rentals

Renovated & Modern Victorian in Historic West End

NEW: Spacious Quaint & Convenient Hideaway!

By The River

The Hangar

The Majestic View | Luxury Stay Golf Views

Prime West Hartford Center Location: Historic Gem

Heart of Hartford

Bright & Private WHOLE HOUSE 4 YOU Near Everything
Private house rentals

Charming Cape Home, Close to All

Serene Apartment in Glastonbury

Lake House Retreat Granby CT

The little house that could!

RiverView Oasis

The Doll House

Farmhouse Broad Brook: Comfort & Charm.

Home near Six Flags/ hot tub
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.ﺇ404 | ﺩ.ﺇ507 | ﺩ.ﺇ544 | 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 30 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 1,110 verified reviews to help you choose

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

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 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
- Groton Long Point Main Beach
- TPC River Highlands
- Brownstone Adventure Sports Park
- Silver Sands Beach
- Bash Bish Falls State Park
- Woodmont Beach
- Kent Falls State Park
- Groton Long Point South Beach
- Catamount Mountain Ski Resort
- Clinton Beach
- Giants Neck Beach
- Grove Beach
- Harveys Beach
- Bushnell Park
- Mystic Seaport Museum
- Bayview Beach
- Brimfield State Forest
- Fort Trumbull Beach
- Hammonasset Beach State Park
- Norman Rockwell Museum