Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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

Guest favourite

Guest suite in Wethersfield

4.99 out of 5 average rating, 247 reviews

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.

Jul. 24 – 31

$187 CAD per night
Guest favourite

Guest suite in Vernon

4.98 out of 5 average rating, 145 reviews

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.

Sep. 10 – 17

$176 CAD per night
Guest favourite

Loft in Tolland

4.98 out of 5 average rating, 148 reviews

Cozy studio loft

Home away from home! In a serene, wooded area tucked away from the road, you'll find our studio loft mother-in-law apartment. Beautiful views with wildlife often spotted. Well-lit with many windows to let in the morning light. Suitable for a change of scenery while working remotely, a brief stay between locations, or your actual destination. UConn is minutes down the road. Looking for antiques? Stafford Speedway? Mohegan Sun or Foxwoods visits? Outdoor enthusiast? This place works for all!

Jan. 8 – 15

$158 CAD per night

Popular amenities for Windsor vacation 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 vacation rentals in Windsor

Guest favourite

Apartment in Ashford

4.99 out of 5 average rating, 218 reviews

Enjoy a Farm Stay without the Work

Nov. 20 – 27

$111 CAD per night
Guest favourite

Guesthouse in Glastonbury

4.96 out of 5 average rating, 133 reviews

Unique luxurious private building in historic area

Aug. 27 – Sep. 3

$270 CAD per night
Guest favourite

Cottage in Granby

4.86 out of 5 average rating, 133 reviews

The Little Red Schoolhouse ~ Circa 1877

Dec. 31 – Jan. 7

$246 CAD per night
Guest favourite

Apartment in Stafford

4.88 out of 5 average rating, 140 reviews

Historic 1 bedroom suite

Dec. 17 – 24

$141 CAD per night
Superhost

Home in Windsor

4.86 out of 5 average rating, 21 reviews

Quiet 3 BRS home with garages

Feb. 26 – Mar. 5

$205 CAD per night
Superhost

Apartment in Windsor Locks

4.86 out of 5 average rating, 88 reviews

Apt near Bradley airport Six Flags with parking

May 9 – 16

$164 CAD per night
Guest favourite

Guest suite in Bloomfield

5.0 out of 5 average rating, 69 reviews

Guest Suite with Private Entrance & View

Dec. 3 – 10

$232 CAD per night
Superhost

Home in South Windsor

4.84 out of 5 average rating, 19 reviews

Grampa Potatoes Homestead

Mar. 5 – 12

$193 CAD per night
Guest favourite

Home in Windsor

4.97 out of 5 average rating, 33 reviews

Relax By The Water

Nov. 2 – 9

$340 CAD per night
Superhost

Apartment in Manchester

4.83 out of 5 average rating, 24 reviews

Luxury 1BR Manchester Oasis Apartment/Downtown

Dec. 2 – 9

$173 CAD per night
Guest favourite

Guest suite in Coventry

5.0 out of 5 average rating, 54 reviews

Get Away Rock Farm “5 Star” Suite UConn Lovely BnB

Jan. 28 – Feb. 4

$170 CAD per night
Guest favourite

Farm stay in Glastonbury

5.0 out of 5 average rating, 50 reviews

Historic Farmhouse by the River (Duplex)

Nov. 5 – 12

$195 CAD per night

Quick stats about vacation rentals in Windsor

Total rentals

60 properties

Wifi availability

60 properties include access to wifi

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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  2. United States
  3. Connecticut
  4. Hartford County
  5. Windsor