Vacation rentals in Windsor

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Windsor

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

Guest favorite

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

G$25,424 GYD per night
Guest favorite

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

G$23,973 GYD per night
Guest favorite

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

G$20,282 GYD 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 favorite

Apartment in Ashford

4.99 out of 5 average rating, 218 reviews

Enjoy a Farm Stay without the Work

Nov 20 – 27

G$15,106 GYD per night
Guest favorite

Guesthouse in Glastonbury

4.96 out of 5 average rating, 133 reviews

Unique luxurious private building in historic area

Aug 27 – Sep 3

G$32,340 GYD per night
Guest favorite

Cottage in Granby

4.86 out of 5 average rating, 133 reviews

The Little Red Schoolhouse ~ Circa 1877

Dec 31 – Jan 7

G$29,820 GYD per night
Guest favorite

Apartment in Stafford

4.88 out of 5 average rating, 140 reviews

Historic 1 bedroom suite

Dec 17 – 24

G$18,217 GYD 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

G$26,063 GYD 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

G$20,570 GYD per night
Guest favorite

Guest suite in Bloomfield

5.0 out of 5 average rating, 69 reviews

Guest Suite with Private Entrance & View

Dec 3 – 10

G$30,174 GYD per night
Superhost

Home in South Windsor

4.84 out of 5 average rating, 19 reviews

Grampa Potatoes Homestead

Mar 5 – 12

G$25,021 GYD per night
Guest favorite

Home in Windsor

4.97 out of 5 average rating, 33 reviews

Relax By The Water

Nov 2 – 9

G$42,595 GYD per night
Superhost

Apartment in Manchester

4.83 out of 5 average rating, 24 reviews

Luxury 1BR Manchester Oasis Apartment/Downtown

Dec 2 – 9

G$19,670 GYD per night
Guest favorite

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

G$22,391 GYD per night
Guest favorite

Farm stay in Glastonbury

5.0 out of 5 average rating, 50 reviews

Historic Farmhouse by the River (Duplex)

Nov 5 – 12

G$26,551 GYD 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

Frequently Asked Questions

  • Do house rentals in Windsor have a kitchen?

    Absolutely! We offer over 30 house rentals with a kitchen in Windsor. Enjoy a tailored experience with all the comforts you desire.

  • How much does it cost to stay in apartment rentals in Windsor?

    Experience the best of Windsor with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • What are the most popular amenities for House Rentals in Windsor?

    Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with free parking, over 30 homes with a kitchen, over 30 homes with air conditioning, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.

  • Do apartment rentals in Windsor have air conditioning?

    Absolutely! We offer over 10 apartment rentals with air conditioning in Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Are there family-friendly vacation rentals in Windsor?

    Windsor has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do apartment rentals in Windsor have wifi?

    Absolutely! We offer over 10 apartment rentals with wifi in Windsor. Enjoy a tailored experience with all the comforts you desire.

  • Are there vacation rentals with a dedicated workspace in Windsor?

    Yes! Work meets play with ease at over 40 vacation rentals in Windsor featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there pet-friendly vacation rentals in Windsor?

    Four-legged friends are welcome in Windsor. Choose from more than 10 vacation rentals for guests traveling with pets.

Destinations to explore

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