Vacation rentals in Windsor

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Top-rated holiday rentals in Windsor

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favourite
Guest suite in Wethersfield
Bright, clean studio in charming Old Wethersfield
Clean, bright studio apartment in the charming village of Old Wethersfield. Stroll to cafes, village green, historic homes and museums. Minutes from I-91 with easy commuting access to downtown Hartford, business and tourist sites, universities, and Hartford Hospital/CCMC. The studio is an in-law suite above our garage. It is attached to our home but has its own keyed entrance. It has a full kitchen, bathroom with shower over tub, closet, queen-sized bed, kitchen table/chairs, and workspace.
22–29 Apr
$220 NZD per night
4.99 out of 5 average rating, 246 reviews
Guest favourite
Guest suite in Vernon
Laura's Loft and Gallery, private suite
Unique and roomy space with private entrance, two bedrooms, full bath with tub shower, and plenty of room to relax. Kitchen space has mini fridge, microwave, toaster oven, hot plate, and crock pot. Pleasant living area opening to 2nd floor deck. WiFi with Ethernet also, great remote work space. Quiet and private, only common area shared with us is first floor entry into breezeway. Free parking on premises. Full coffee setup for your breakfast included, and homemade scones in seasonal flavors.
3–10 Aug
$222 NZD per night
4.98 out of 5 average rating, 145 reviews
Guest favourite
Guesthouse in Glastonbury
Unique luxurious private building in historic area
Unique private space for sophisticated adult(s). Located just 7 miles from downtown Hartford, 1 mile from Route 2 & 84/91 interchange. Guests may relax in this completely renovated historic Barn, with covered parking, away from street view. Enjoy this luxurious space and the private gym which includes treadmill, eliptical, bike, free weights, boxing bags, and yoga space. Upstairs, walk the catwalk between spacious bedroom and full sized Office / Loft over looking historic Main Street.
25 Apr – 2 May
$320 NZD per night
4.96 out of 5 average rating, 133 reviews

Popular amenities for Windsor holiday rentals

Stay near Windsor's top sights

Tunxis Grill & Pizzeria5 locals recommend
Price Chopper15 locals recommend
Copaco Shopping Center3 locals recommend
Republic Restaurant3 locals recommend
Windsor Asian Bistro3 locals recommend
Budget Car Rental3 locals recommend

Other great holiday rentals in Windsor

Guest favourite
Loft in Hartford
Loft - Queen Anne Row House in a historic district
17–24 Feb
$190 NZD per night
4.98 out of 5 average rating, 522 reviews
Guest favourite
Guesthouse in Glastonbury
Charming Barn Apartment
28 May – 4 Jun
$282 NZD per night
4.91 out of 5 average rating, 171 reviews
Superhost
Apartment in Windsor Locks
Apt near Bradley airport Six Flags with parking
3–10 May
$198 NZD per night
4.86 out of 5 average rating, 85 reviews
Guest favourite
Home in Windsor
Relax By The Water
18–25 Aug
$374 NZD per night
4.97 out of 5 average rating, 33 reviews
Guest favourite
Guest suite in Bloomfield
Guest Suite with Private Entrance & View
27 Jul – 3 Aug
$269 NZD per night
5.0 out of 5 average rating, 68 reviews
Guest favourite
Home in Windsor
Hilltop RiverView Retreat
2–9 Jan
$549 NZD per night
4.94 out of 5 average rating, 69 reviews
Guest favourite
Home in Windsor
Quiet 3 BRS home with garages
25 Sep – 2 Oct
$287 NZD per night
4.86 out of 5 average rating, 21 reviews
Superhost
Home in Windsor
Island Vibes
6–13 Oct
$394 NZD per night
4.83 out of 5 average rating, 24 reviews
Guest favourite
Farm stay in Glastonbury
Rustic Farmhouse by the River (Duplex)
20–27 Mar
$229 NZD per night
4.98 out of 5 average rating, 50 reviews
Guest favourite
Home in South Windsor
Grampa Potatoes Homestead
31 Aug – 7 Sep
$252 NZD per night
4.89 out of 5 average rating, 18 reviews
Guest favourite
Home in Bloomfield
Spacious Charming New England Cape
24–31 Aug
$848 NZD per night
4.94 out of 5 average rating, 88 reviews
Guest favourite
Apartment in New Britain
Spacious Cozy Guest Suite
16–23 Nov
$179 NZD per night
4.96 out of 5 average rating, 79 reviews

Quick stats about holiday rentals in Windsor

Total rentals

60 properties

Wi-Fi availability

60 properties include access to Wi-Fi

Rentals with dedicated workspaces

40 properties have a dedicated workspace

Pet-friendly rentals

10 properties allow pets

Family-friendly rentals

20 properties are a good fit for families

Total number of reviews

2.1K reviews

Destinations to explore

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  3. Connecticut
  4. Hartford County
  5. Windsor