Vacation rentals in Windsor

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Top-rated vacation rentals in Windsor

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Guest favorite

Guest suite in Wethersfield

4.99 out of 5 average rating, 251 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.

May 31 – Jun 7

R2,311 ZAR per night

Guest favorite

Guest suite in Vernon

4.98 out of 5 average rating, 146 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.

Oct 5 – 12

R2,125 ZAR per night

Guest favorite

Guesthouse in Glastonbury

4.96 out of 5 average rating, 133 reviews

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.

Sep 5 – 12

R2,550 ZAR per night

Superhost

Apartment in Windsor Locks

4.86 out of 5 average rating, 93 reviews

Apt near Bradley airport Six Flags with parking

Enjoy your stay at a stylish and cozy apt. No shared or common areas other then the parking space. Renting out the whole upstairs apartment. There is no longer a dog on the property. Direct access into the apartment through the back, up the outdoor staircase. It's a short drive to the Bradley International Airport. (10 min) Bedroom has a Queen bed with fresh linens. Fully stocked kitchen: stove, oven, fridge, complimentary tea and coffee. Pots, pans, baking dishes, utensils, salt pepper.

Jul 4 – 11

R1,882 ZAR per night

Guest favorite

Home in Manchester

4.94 out of 5 average rating, 174 reviews

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.

Dec 18 – 25

R1,888 ZAR per night

Guest favorite

Loft in Hartford

4.98 out of 5 average rating, 529 reviews

Loft - Queen Anne Row House in a historic district

Hosted by Judy and Greg, our home is close to art, culture, live theater, and restaurants. Our home is also close to major insurance companies, the state capitol and state of Connecticut offices. You’ll love the cozy 3rd floor loft. We also offer off street parking. Garage space is also available as an option. Our home is a perfect destination for couples, solo adventurers, and business travelers.

Jan 2 – 9

R2,138 ZAR per night

Guest favorite

Guest suite in East Granby

4.84 out of 5 average rating, 273 reviews

Staying at Ten Hillcrest

What I’ve always thought of as the perfect location! Private enough to see trees and birds and yet close enough to jump on the highway to anywhere. Conveniently located on a dead end street with no through traffic. On your way out take a left and head towards farm and eateries or take a right and head to the city of Hartford or Springfield. Just minutes from Bradley International Airport

Jun 21 – 28

R2,376 ZAR per night

Guest favorite

Guesthouse in Glastonbury

4.91 out of 5 average rating, 171 reviews

Charming Barn Apartment

Our one bedroom apartment in a colonial barn has a country feeling but is a 10 minute drive into downtown Hartford, and halfway between Boston and New York City .There are woods on one side and from the living area look out on a hillside where you can sit for a spell or spend some time on the private stone patio right outside the door. There are beaches and casinos within an hours drive.

May 12 – 19

R2,636 ZAR per night

Guest favorite

Guesthouse in Granby

4.99 out of 5 average rating, 704 reviews

Windy Top Cottage ~ A Romantic "European" Getaway

The Windy Top Cottage is an old stone building constructed in 1932 by H. L. Bitter, a wealthy Hartford businessman. This area of Granby was a favorite of the Hartford elite for a place to 'summer' in the early part of the 20th Century. The cottage was the quarters for the domestic staff while the family was in North Granby. With an elevation of 970, we offer clean, fresh country air!

Dec 29 – Jan 5

R3,101 ZAR per night

Guest favorite

Cottage in Granby

4.87 out of 5 average rating, 137 reviews

The Little Red Schoolhouse ~ Circa 1877

This wonderful old building is listed on the National Register of Historic Places and operated as the District 9 schoolhouse until 1948. Now, this beautiful piece of history is available for you to enjoy! Located in the picturesque West Granby, Connecticut, this little schoolhouse directly abuts hundreds of acres of open space, Granby Land Trust property, and several organic farms.

Feb 21 – 28

R2,729 ZAR per night

Guest favorite

Farm stay in Granby

4.89 out of 5 average rating, 238 reviews

The Farmhouse at Maple View Farm

Sunny, vintage 1936 farmhouse in the center of a quintessential New England farm town. Maple View Farm is a working livestock farm with horses, ponies, pigs and chickens plus a big garden. Wake up to the sounds of the rooster and step outside to pet the horses and ponies. Our on-farm Brewery (check hours) uses local ingredients. Window A/C units in bedrooms.

Dec 24 – 31

R2,997 ZAR per night

Guest favorite

Apartment in Enfield

4.99 out of 5 average rating, 140 reviews

FROG Suite Apartment

Welcome to the FROG Suite apartment, the prefect place in a comfy private space. Be it for work, pleasure, travel or leisure, this alluring updated space is located upstairs over the garage in a quiet residential neighborhood and includes a private keyless entry door lock. Apartment is located upstairs over the garage and is attached to the house.

Mar 3 – 10

R1,932 ZAR per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Windsor vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

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

Superhost

Home in Windsor

4.86 out of 5 average rating, 21 reviews

Quiet 3 BRS home with garages

Feb 2 – 9

R2,385 ZAR per night

Guest favorite

Guest suite in Bloomfield

5.0 out of 5 average rating, 71 reviews

Guest Suite with Private Entrance & View

Jan 29 – Feb 5

R2,784 ZAR per night

Superhost

Apartment in East Windsor

4.86 out of 5 average rating, 14 reviews

Modern Cozy Studio

Dec 3 – 10

R2,198 ZAR per night

Guest favorite

Home in Windsor

4.97 out of 5 average rating, 34 reviews

Relax By The Water

Feb 18 – 25

R3,898 ZAR per night

Superhost

Home in South Windsor

4.84 out of 5 average rating, 19 reviews

Grampa Potatoes Homestead

Dec 6 – 13

R2,672 ZAR per night

Guest favorite

Guest suite in Bloomfield

4.91 out of 5 average rating, 68 reviews

Private Cozy Suite - Zero Fees - EV Charger

Nov 18 – 25

R1,957 ZAR per night

Guest favorite

Home in Windsor

4.94 out of 5 average rating, 71 reviews

Hilltop RiverView Retreat

Feb 25 – Mar 4

R5,262 ZAR per night

Superhost

Farm stay in Bloomfield

4.8 out of 5 average rating, 10 reviews

Auerfarm Farmstay Baldwin Cottage (169)

Sep 27 – Oct 4

R2,445 ZAR per night

Show all

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
1.9K 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.
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 wifi, over 30 homes with air conditioning, over 30 homes with free parking, over 30 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Windsor have air conditioning?
Absolutely! We offer over 30 house 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 house rentals in Windsor have wifi?
Absolutely! We offer over 30 house 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.
Do house rentals in Windsor have free parking?
Absolutely! We offer over 30 house rentals with free parking in Windsor. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Windsor

Top-rated vacation rentals in Windsor

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Windsor vacation rentals

Stay near Windsor's top sights

Other great vacation rentals in Windsor

Home in Windsor

Guest suite in Bloomfield

Apartment in East Windsor

Home in Windsor

Home in South Windsor

Guest suite in Bloomfield

Home in Windsor

Farm stay in Bloomfield

Quick stats about vacation rentals in Windsor

Total rentals

Wifi availability

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

Do house rentals in Windsor have a kitchen?

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

Do house rentals in Windsor have air conditioning?

Are there family-friendly vacation rentals in Windsor?

Do house rentals in Windsor have wifi?

Are there vacation rentals with a dedicated workspace in Windsor?

Are there pet-friendly vacation rentals in Windsor?

Do house rentals in Windsor have free parking?

Destinations to explore