Windsor Holiday Rentals, Connecticut: Private House Rentals

A rustic barn surrounded by autumn foliage and a field.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Go beyond your typical stay in Windsor

Pet friendly

Pool

Apartment

Hot tub

Condo

Family friendly

Cottage

Waterpark

Check prices for these dates

Tonight

Tomorrow

This weekend

Next weekend

Our top choices for Windsor hotels

A modern hotel lobby with a long bar, seating area, and a TV mounted on the wall.

An indoor swimming pool with clear water, surrounded by lounge chairs and a table.

A hotel room with a modern design, featuring a large bed, two armchairs with cushions, a flat-screen TV mounted on the wall, and a carpeted floor.

A modern hotel room with a flat-screen TV mounted on the wall, a grey armchair with a yellow pillow, a round ottoman, a grey sofa with yellow pillows, and a side table with a lamp and remote control.

1. Marriott Hartford/Windsor Airport

Windsor

Normand

4.392.986 ₫

5.051.934 ₫ total

includes taxes & fees

30 Oct - 31 Oct

A modern hotel room with a dining area, seating arrangements, and a large TV screen.

An indoor swimming pool area with tiled flooring, lounge chairs, and tables with umbrellas.

A modern living room with a grey sofa, a black exercise bike, and a large mirror reflecting the room.

A hotel room with a large bed, a desk, a chair, and a sofa.

2. Hampton Inn Hartford/Airport

Windsor

Angela

3.367.783 ₫

3.872.951 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern living room with grey sofas, blue ottomans, and a large plant.

A modern restaurant with a long counter, bar area, and seating for 20 people.

A modern kitchen with a central island, bar stools, and pendant lighting.

An indoor swimming pool with a tiled floor, a brick wall, and a glass partition.

3. HYATT house Hartford North/Windsor

Windsor

Trisha

3.509.190 ₫

4.035.569 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A living room with a fireplace, comfortable seating, and a flat-screen TV mounted above the fireplace.

A hotel corridor with a carpeted floor, a sofa, and a sign indicating room number.

A multi-story hotel with a brick facade, green roof, and a covered entrance.

A bar area with a granite countertop, bar stools, and a television above the bar.

4. Hilton Garden Inn Hartford North/Bradley Int'l Airport

Windsor

James

3.224.296 ₫

3.707.940 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel room with a sofa, armchair, and a TV mounted on the wall.

An outdoor seating area with wicker furniture and a small table with a drink.

A dark-themed room with a refrigerator stocked with beverages and a shelf unit with snacks and toiletries.

A bar area with a counter, stools, and a menu board.

5. Courtyard By Marriott Hartford/Windsor Airport

Windsor

Chelsea

3.645.196 ₫

4.191.975 ₫ total

includes taxes & fees

22 Oct - 23 Oct

A brick building with a sign reading "Marriott Residence Inn" at the entrance, surrounded by landscaped greenery and a gated driveway.

A hotel room with a bed, a desk with a television, a chair, and a sofa.

A kitchenette with a wooden shelf unit labeled 'market' stocked with snacks and a refrigerator with beverages.

A residential neighborhood with houses, well-maintained lawns, and a clear pathway.

6. Residence Inn by Marriott Hartford/Windsor

Windsor

elizabeth

4.185.034 ₫

4.812.789 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A modern hotel lobby with a breakfast bar, a seating area, and a view of the outdoors.

A modern lounge area with a sofa, armchairs, a flat-screen TV, and a decorative wall.

A reception area with a cityscape mural, two reception desks, and a tiled floor.

7. La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

Windsor Locks

Robin

2.595.241 ₫

2.984.528 ₫ total

includes taxes & fees

18 Oct - 19 Oct

An indoor swimming pool with clear glass walls, a blue pool area, and sunlit seating areas.

A modern reception area with a digital display, a reception desk, and a seating area with patterned ottomans.

A DoubleTree by Hilton hotel with a 'Shade Grill' sign, a well-maintained lawn, and a clear sky at dusk.

A bar area with high stools, a counter, and a television mounted on the wall.

8. DoubleTree by Hilton Hartford - Bradley Airport

Windsor Locks

Soleil

3.204.540 ₫

3.685.221 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A hotel patio with outdoor seating, a fire pit, and a building with multiple floors and large windows.

A modern kitchen with a bar area, seating, and a view of the outdoors.

A multi-story hotel with a modern design, featuring a prominent entrance and a covered walkway.

A modern hotel lobby with a marble reception desk, bar seating, and a large seating area with sofas and chairs.

9. Cambria Hotel Manchester South Windsor

South Windsor

Rosa

3.513.089 ₫

4.040.052 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A buffet setup with various food options, a glass partition, and a modern chandelier.

A spacious lobby with a curved sofa, a reception desk, and a fireplace.

A hotel kitchenette with a marble countertop, a hanging light fixture, and two refrigerators labeled 'Homewood Suites by Hilton'.

A hotel room with a kitchenette, a bed, a TV, a seating area, and a large window.

10. Homewood Suites by Hilton Windsor Locks Hartford

Windsor Locks

Matthew

3.017.903 ₫

3.470.588 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A lobby with a fireplace, seating area, and a reception desk.

A modern lobby with a blue sofa, a round coffee table, and a leather chair.

A room with a fireplace, a wooden table with a bottle of champagne, two glasses, and a bouquet of roses.

11. Fairfield Inn & Suites Hartford Airport

Windsor Locks

Bettie

2.722.092 ₫

3.130.406 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel with a flat roof, large windows, and a covered entrance.

A hotel room with a bed, a desk, a chair, a sofa, a microwave, and a coffee machine.

A modern lobby with a reception desk, seating area, and a large wall-mounted screen.

A breakfast buffet with various food items and condiments.

12. Springhill Suites Marriott Airport

Windsor Locks

Gary

3.251.849 ₫

3.739.626 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel lobby with seating arrangements, a central dining table, and a kitchenette area.

A hotel room with a large window, a sofa, a chair, a small table, a TV, and a chessboard.

A hotel room with two beds, a desk, a chair, a TV, a lamp, a small table with bottles, and a framed picture on the wall.

A reception desk with a wooden backdrop and a large, detailed drawing of a ship.

13. Sheraton Hartford Hotel at Bradley Airport

Windsor Locks

margaret

6.606.375 ₫

7.597.332 ₫ total

includes taxes & fees

31 Oct - 1 Nov

A hotel lobby with a long communal table, several chairs, a sofa, and a television.

A snack display with a 'Grab a Snack' sign and a 'Welcome to Hartford Manchester' sign above it.

An indoor swimming pool with clear blue water, surrounded by lounge chairs and a lifeguard sign indicating no diving.

An outdoor patio with a table and chairs, a large umbrella, and a view of a building with large windows.

14. Hampton Inn & Suites Hartford-Manchester

Manchester

SeongSu

2.749.645 ₫

3.162.091 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A Holiday Inn Express hotel with a covered entrance, multiple floors, and a landscaped driveway.

A coffee station with two espresso machines, a coffee grinder, and various coffee-related items.

A buffet with labeled trays of turkey sausage and cookies.

An indoor swimming pool with clear water, a lifeguard chair, and a changing room with a shower.

15. Holiday Inn Express & Suites Bradley Airport by IHG

Windsor Locks

Frank

3.171.268 ₫

3.646.958 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A Candlewood Suites hotel with a modern design, featuring multiple floors and a well-lit entrance.

A kitchen with a large island, a microwave, cabinets, and a refrigerator.

A hotel room with a sofa, a bed, a desk, and a framed picture on the wall.

A playground with swings, a basketball hoop, and a shelter.

16. Candlewood Suites Windsor Locks Bradley Arpt by IHG

Windsor Locks

Ashley

2.287.472 ₫

2.630.593 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A hotel hallway with a bed, desk, and a mirror.

A hotel room with a kitchenette, a bed, a desk, and a TV.

A long, narrow hotel corridor with carpeted floors, wooden trim, and wall-mounted lights.

A spacious hotel lobby with a wooden herringbone floor, a reception desk, and a large glass door leading outside.

17. Comfort Inn East Windsor - Springfield

East Windsor

Lovett

2.688.040 ₫

3.091.246 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A hotel room with a large window, a flat-screen TV, red upholstered chairs, a glass coffee table, and a patterned carpet.

A Days Inn hotel with a two-story building, a covered patio, and a landscaped front yard.

A spacious dining area with high ceilings and large windows, featuring red upholstered chairs and a glass-top table.

A Days Inn van parked at a gas station with a clear view of the sky and distant buildings.

18. Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

Windsor Locks

Caroline

2.099.016 ₫

2.413.868 ₫ total

includes taxes & fees

8 Oct - 9 Oct

An outdoor patio with a stone wall, a grill, and outdoor furniture.

A modern living room with a stone fireplace, a beige sectional sofa, a round coffee table, and a large abstract painting on the wall.

A spacious lobby with a seating area, a stone accent wall, and a television mounted on the wall.

A hotel reception area with a wooden reception desk, framed pictures on the wall, and a 'Hilton Honors' sign.

19. Homewood Suites by Hilton Hartford Manchester

Manchester

Amy

3.603.028 ₫

4.143.482 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A Baymont Inn & Suites with a prominent sign, brick buildings, and a landscaped entrance area.

A gym with various exercise equipment, a clock on the wall, and large windows.

A Baymont Inn & Suites reception area with a television, two potted plants, a fireplace, and a leather couch.

A hotel room with a large bed, bedside tables, a desk, a chair, and a television.

20. Baymont by Wyndham East Windsor Bradley Airport

East Windsor

Samuel

1.744.277 ₫

2.005.907 ₫ total

includes taxes & fees

20 Oct - 21 Oct

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Stay near popular Windsor attractions

Loomis Chaffee School

This prestigious New England boarding school blends historic architecture with state-of-the-art facilities. Schedule a guided campus tour to experience Loomis Chaffee's innovative learning spaces and picturesque grounds.

See properties

Northwest Park

7.8/10 (24 reviews)

Explore 473 acres of diverse habitats through 12 miles of scenic trails at this natural retreat. The nature center's educational exhibits and heritage breed farm create an immersive outdoor experience for all ages.

See properties

Oliver Ellsworth Homestead

8.2/10 (15 reviews)

Step back in time at Elmwood, home of Oliver Ellsworth who helped draft the US Constitution. Explore period furnishings and family artefacts in this beautifully preserved 18th-century residence.

See properties

Windsor Arts Center

7.6/10 (18 reviews)

This historic freight house turned art centre showcases contemporary New England art in a charming railway setting. Enjoy rotating exhibitions while soaking in the creative atmosphere of Windsor's cultural hub.

See properties

Windsor Historical Society

8.0/10 (12 reviews)

Step into Connecticut's oldest English settlement at the Windsor Historical Society's museum complex. Explore two historic homes dating to the 1700s and try on colonial costumes in the hands-on learning centre.

See properties

Vintage Radio and Communications Museum of Connecticut

7.6/10 (13 reviews)

This time-traveling museum showcases communication technology from the 1800s to modern computers. Tap out Morse code messages and tune vintage radios while knowledgeable volunteers bring history to life.

See properties

Windsor Meadows State Park

7.6/10 (10 reviews)

This riverside haven offers peaceful trails winding through floodplain forests with Connecticut River views. Explore the meadows or launch your boat for a day of fishing and serene water adventures.

See properties

Learn more about Windsor

Stroll through centuries of history at the Oliver Ellsworth Homestead, where a Founding Father's legacy comes alive. Explore nature trails and farm animals at Northwest Park, then catch an outdoor concert at SummerWind's scenic amphitheatre.

See all hotels in Windsor

Top Windsor Hotel Reviews

Holiday Inn Express Springfield Downtown by IHG

8/10 Good

"The room was clean and comfortable"

Quality Inn West Springfield

10/10 Excellent

"Great!"

Hilton Garden Inn Hartford North/Bradley Int'l Airport

8/10 Good

"The bar in the hotel lobby is awesome!"

MGM Springfield

10/10 Excellent

"Clean"

Marriott Hartford/Windsor Airport

10/10 Excellent

"Comfort of bed and pillows. Great shower. Bar tender wasn’t the most pleasant but she made a good margarita."

Residence Inn by Marriott Hartford/Windsor

8/10 Good

"Hotel was adequate for our needs."

The Capitol Hotel

10/10 Excellent

"I know there were mixed reviews about this establishment however it was very nice. I went with my mother for the weekend. The staff was friendly and very helpful. The parking at the hotel is $15/night. The Wifi is complimentary as well as the breakfast. It is maybe a 5 minute walk to Pratt District and other areas of downtown Hartford. The room was clean and comfortable. The room had a microwave and refrigerator which was nice. For those that are light sleepers you could hear people outside your room but it did not matter to me. I would stay here again."

Blue A Modern Hotel, an Ascend Collection Hotel

10/10 Excellent

"Clean and modern. Massage chair in each room is a bonus. Kevin was very helpful and walked us up to our room."

More cheap stays in Windsor

Rodeway Inn & Suites East Windsor

161 Bridge St East Windsor CT

1.517.270 ₫

1.744.861 ₫ total

19 Oct - 20 Oct

includes taxes & fees

5.4/10 (1,005 reviews)

Motel 6 Enfield, CT - Hartford

11 Hazard Ave Enfield CT

1.524.288 ₫

1.753.035 ₫ total

7 Oct - 8 Oct

includes taxes & fees

Candlewood Suites Windsor Locks Bradley Arpt by IHG

149 Ella Grasso Turnpike Windsor Locks CT

2.287.472 ₫

2.630.593 ₫ total

2 Nov - 3 Nov

includes taxes & fees

Holiday Inn Express Springfield Downtown by IHG

145 State Street Springfield MA

2.596.801 ₫

2.946.071 ₫ total

3 Nov - 4 Nov

includes taxes & fees

9/10 Wonderful! (1,323 reviews)

Holiday Inn Express Southington by IHG

120 Laning St Southington CT

2.585.103 ₫

2.972.869 ₫ total

1 Nov - 2 Nov

includes taxes & fees

8.6/10 Excellent! (1,458 reviews)

Hampton Inn West Springfield

1011 Riverdale St West Springfield MA

3.175.947 ₫

3.634.871 ₫ total

1 Nov - 2 Nov

includes taxes & fees

Hotels in Windsor with star rating

Frequently asked questions

What's the seasonal weather in Windsor?

The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of 0°C. The snowiest months in Windsor are January, February, March and April, with each month seeing an average of 15 cm of snowfall.

Explore a world of travel with Expedia

Rental cars Bradley Intl. airport

Book Hotels in Windsor on Expedia.com

Find hotels in Windsor, CT from 1.744.861 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Windsor

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Windsor hotels

1. Marriott Hartford/Windsor Airport

2. Hampton Inn Hartford/Airport

3. HYATT house Hartford North/Windsor

4. Hilton Garden Inn Hartford North/Bradley Int'l Airport

5. Courtyard By Marriott Hartford/Windsor Airport

6. Residence Inn by Marriott Hartford/Windsor

7. La Quinta Inn & Suites by Wyndham Hartford - Bradley Airport

8. DoubleTree by Hilton Hartford - Bradley Airport

9. Cambria Hotel Manchester South Windsor

10. Homewood Suites by Hilton Windsor Locks Hartford

11. Fairfield Inn & Suites Hartford Airport

12. Springhill Suites Marriott Airport

13. Sheraton Hartford Hotel at Bradley Airport

14. Hampton Inn & Suites Hartford-Manchester

15. Holiday Inn Express & Suites Bradley Airport by IHG

16. Candlewood Suites Windsor Locks Bradley Arpt by IHG

17. Comfort Inn East Windsor - Springfield

18. Days Inn by Wyndham Windsor Locks / Bradley Intl Airport

19. Homewood Suites by Hilton Hartford Manchester

20. Baymont by Wyndham East Windsor Bradley Airport

Stay near popular Windsor attractions

Loomis Chaffee School

Northwest Park

Oliver Ellsworth Homestead

Windsor Arts Center

Windsor Historical Society

Vintage Radio and Communications Museum of Connecticut

Windsor Meadows State Park

Learn more about Windsor

Top Windsor Hotel Reviews

Holiday Inn Express Springfield Downtown by IHG

Quality Inn West Springfield

Hilton Garden Inn Hartford North/Bradley Int'l Airport

MGM Springfield

Marriott Hartford/Windsor Airport

Residence Inn by Marriott Hartford/Windsor

The Capitol Hotel

Blue A Modern Hotel, an Ascend Collection Hotel

More cheap stays in Windsor

Rodeway Inn & Suites East Windsor

Motel 6 Enfield, CT - Hartford

Candlewood Suites Windsor Locks Bradley Arpt by IHG

Holiday Inn Express Springfield Downtown by IHG

Holiday Inn Express Southington by IHG

Hampton Inn West Springfield

Hotels in Windsor with star rating

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app