Windsor Holiday Homes from €111: Search Top House Rentals

Windsor Holiday Homes
Connecticut
United States of America
Holiday Homes
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Our top choices for Windsor holiday homes

A two-story house with a red front door, stone steps, and two deer statues.

A spacious kitchen with wooden cabinets, a large island, and a dining area with chairs and a rug.

1. Spacious Yard w/ Gazebo: Charming Windsor Retreat

Spacious Yard w/ Gazebo: Charming Windsor Retreat

Windsor

9.4 out of 10, Exceptional, (13 reviews)

9.4/10

Exceptional

(13 reviews)

"The place is easy to locate. It is as beautiful as the photo. Clean and spacious.I definitely would stay there again."

Delores N.

The price is €657

€657

includes taxes & fees

23 Nov - 24 Nov

Spacious Yard w/ Gazebo: Charming Windsor Retreat

A modern living room with a sofa, a coffee table, and a rug.

A house with a brick patio and a window with a screen.

A wooden deck with a table and two chairs, surrounded by a white railing.

A modern living room with a sofa, coffee table, and a TV mounted on the wall.

2. Entire guest suite in South Windsor, Connecticut

Entire guest suite in South Windsor, Connecticut

South Windsor

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"Good location"

Arthur

The price is €111

€111

includes taxes & fees

2 Nov - 3 Nov

Entire guest suite in South Windsor, Connecticut

A room with a large potted tree, a wooden cabinet, a round table, and a sofa with a cushion.

A dining table with a decorative centerpiece, surrounded by chairs, in a room with large windows.

A circular stone fire pit surrounded by four wicker chairs.

A spacious living room with hardwood flooring, a fireplace, a television, and a large window.

3. The Serene Skyway Retreat

The Serene Skyway Retreat

Windsor Locks

9.0 out of 10, Wonderful, (18 reviews)

9.0/10

Wonderful

(18 reviews)

"Very clean, the host was very responsive in a timely manner. The location was a nice suburban neighborhood, huge yard, on the end of a cul-de-sac. The kids loved the pool table & downstairs apartment. There are lots of stairs so maybe not the best for an older person, but they did have a ramp entry into the house. The house was very nicely decorated and comfortable furnishings."

Jeanne J.

The price is €289

€289

includes taxes & fees

22 Nov - 23 Nov

The Serene Skyway Retreat

A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, and a stove. There is a dining table with chairs and a coffee maker on the table.

A narrow hallway with wooden flooring and white walls, leading to a door at the end.

A dining area with a marble floor, a wooden table, and six white chairs. A rustic sign with the text 'The HANGAR' is mounted on the wall.

A bedroom with a bed, bedside table, and a small stool.

4. Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

Windsor Locks

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"Great location for our six flags visit (about 15 minutes away)."

Stacey B.

The price is €422

€422

includes taxes & fees

15 Nov - 16 Nov

Welcome to The Hangar, a newly remodeled travel-themed stay, 4 minutes from BDL.

A modern living room with a flat-screen TV, a glass coffee table, and a staircase leading to another level.

A living room with a chandelier, two sofas, a coffee table, and a large window.

A modern kitchen with white cabinets, a stainless steel refrigerator, and a dining area with a glass table and black and white chairs.

A hallway with a white door, a shelf with decorative items, and a view of an orange wall.

5. Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

Manchester

9.2 out of 10, Wonderful, (31 reviews)

9.2/10

Wonderful

(31 reviews)

"Was a great stay"

John S.

Modern ~ 3 Bedroom House ~ Sleeps 8 ~ 11 mins to Hartford

A living room with a staircase, red and grey sofas, a coffee table, and a red door.

A bedroom with a bed, a window with curtains, and artwork on the wall.

A modern office space with a round table, a grey office chair, a red chair, a floor lamp, and a window with sheer curtains.

A modern kitchen with white cabinets, stainless steel appliances, and a black countertop.

6. Modern & Cozy Cape | 4 Bedroom House | Central Location

Modern & Cozy Cape | 4 Bedroom House | Central Location

Manchester Center

9.8 out of 10, Exceptional, (10 reviews)

9.8/10

Exceptional

(10 reviews)

"Great place"

John S.

The price is €269

€269

includes taxes & fees

1 Nov - 2 Nov

Modern & Cozy Cape | 4 Bedroom House | Central Location

A modern dining area with a marble table, white chairs, and a chandelier.

A kitchen with a wooden drawer unit containing kitchen utensils and a pot.

A hallway with wooden flooring leading to a bedroom with a bed and a window.

A living room with a beige sofa, a glass coffee table, a fireplace, and artwork on the walls.

7. Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford

Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford

Manchester

9.2 out of 10, Wonderful, (5 reviews)

9.2/10

Wonderful

(5 reviews)

"House was great for our family stay!"

Kim A.

The price is €287

€287

includes taxes & fees

1 Nov - 2 Nov

Comfy Nest ~ 3BR Sleeps 7 ~ 15 mins to Hartford

A modern kitchen with white cabinets, stainless steel appliances, and a wooden floor.

8. Prime West Hartford Center | Timeless Charm

Prime West Hartford Center | Timeless Charm

West Hartford

10.0 out of 10, Exceptional, (27 reviews)

10/10

Exceptional

(27 reviews)

"Great location and lots of room for grandkids to spread out and fun games for them to play with"

Michael W.

The price is €463

€463

includes taxes & fees

3 Nov - 4 Nov

Prime West Hartford Center | Timeless Charm

A circular stone fire pit surrounded by large rocks and gravel, set in a forested area.

A small white cabin with a porch, surrounded by blooming pink trees.

A spacious living room with a large beige sectional sofa, a round coffee table, and a potted plant.

A lakeside view with a sunset, trees, and a dock with chairs.

9. Sun Filled Lake House Living

Sun Filled Lake House Living

Avon

6.6 out of 10, (4 reviews)

6.6/10

(4 reviews)

"Enjoyed my stayConvenient location for restaurants, shopping etcHome was clean and neat and in a nice quiet neighborhood Good value"

Joseph C.

The price is €242

€242

includes taxes & fees

17 Nov - 18 Nov

Sun Filled Lake House Living

A living room with a blue sofa, a round coffee table, and a staircase.

A living room with a sofa, coffee table, and TV. There is a kitchen visible in the background.

A kitchen with wooden cabinets, a granite countertop, a built-in oven, and a coffee maker.

A bedroom with a wooden bed, two bedside tables, a nightstand, a radiator, and a window with sheer curtains.

10. The Game House Arcade | West Hartford

The Game House Arcade | West Hartford

West Hartford

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Great location and well equipped. We will be back"

Mike W.

The price is €382

€382

includes taxes & fees

1 Nov - 2 Nov

The Game House Arcade | West Hartford

A covered porch with white rocking chairs and a table, a blue ceiling, and a view of the garden.

A living room with a beige sofa, a recliner, a coffee table, a TV stand, and a dining area with a table and chairs.

A dining room with a wooden table, six chairs, a chandelier, and large windows with sheer curtains.

A modern kitchen with stainless steel appliances, white cabinetry, and a large window providing natural light.

11. Charming New England Home in West Hartford Center

Charming New England Home in West Hartford Center

West Hartford

10.0 out of 10, Exceptional, (32 reviews)

10/10

Exceptional

(32 reviews)

"Great location. Beautiful, comfortable home."

karen

The price is €470

€470

includes taxes & fees

1 Nov - 2 Nov

Charming New England Home in West Hartford Center

A modern living room with a grey sectional sofa, a coffee table, decorative mirrors, and a flat-screen TV mounted on the wall.

A hallway with a wooden door, a gray couch, a dining table with chairs, and a trash can.

A spacious room with a grey carpet, a grey sofa, and a basketball hoop.

A modern kitchen with white cabinets, a stainless steel stove, and a black countertop.

12. Red Door Retreat

Red Door Retreat

Vernon

Red Door Retreat

A covered patio with a dining table, chairs, and a grill.

A modern living room with a grey sectional sofa, a round coffee table, and white side tables.

A two-story house with a stone pathway leading to a wooden staircase.

A staircase with wooden steps and black railings, a desk with a chair, and a fireplace with a green mantle.

13. Prime West Hartford Center Location | Historic Gem

Prime West Hartford Center Location | Historic Gem

West Hartford

10.0 out of 10, Exceptional, (37 reviews)

10/10

Exceptional

(37 reviews)

"We loved being so close to downtown West Hartford. The house had everything we needed for a fun graduation weekend."

Trish

The price is €708

€708

includes taxes & fees

23 Nov - 24 Nov

Prime West Hartford Center Location | Historic Gem

A white building with a porch and a stone border.

A kitchen with dark cabinets, a stainless steel oven, a wooden countertop, and a white rug.

A room with a bed, a bookshelf, a TV, a fireplace, and a door leading to another room.

A living room with a sofa, coffee table, and a ceiling fan.

14. Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

Somers

9.8 out of 10, Exceptional, (12 reviews)

9.8/10

Exceptional

(12 reviews)

"Fantastic host. Went out of their way to make our stay very pleasant. Beautiful historic home that felt very welcoming and cozy even though it is so big!"

John

The price is €326

€326

includes taxes & fees

2 Nov - 3 Nov

Spacious 2,000 Sq Ft New England Retreat - 2BR/2BA Walk to Shops and Restaurants

A patio area with wicker furniture and a brick floor.

A wooden dining table with a glass bowl of oranges, a vase with tulips, and a radiator in the background.

A spacious living area with a sofa, a coffee table, and a patterned rug.

A modern kitchen with white cabinets, stainless steel appliances, and a central island with chairs.

15. The Old Avon 1800 Manor

The Old Avon 1800 Manor

Avon

7.0 out of 10, Good, (2 reviews)

7.0/10

Good

(2 reviews)

"Wonderful place and host very responsive and friendly!"

Anonymous traveller

The price is €419

€419

includes taxes & fees

9 Nov - 10 Nov

The Old Avon 1800 Manor

A modern kitchen with stainless steel appliances, a wooden dining table, and a ceiling fan.

A single-story house with a red front door, white siding, and a brick chimney.

A covered outdoor seating area with a table and chairs, surrounded by a wooden fence and potted plants.

A room with a foosball table, a large wall mural, and a basketball hoop.

16. Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags

Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags

West Springfield

The price is €293

€293

includes taxes & fees

30 Oct - 31 Oct

Red Door Retreat West Springfield 3 bedroom w/ Game Room! Near Big E & Six Flags

A living room with a fireplace, sofa, coffee table, and a television mounted on the wall.

A dining room with a long wooden table, chairs, and a chandelier.

17. Lakefront Property with Scenic View - All Seasons!

Lakefront Property with Scenic View - All Seasons!

Enfield

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"My family and I stayed in this lovely cottage the night before our son’s graduation from UConn (approx 49 mins from campus). It was very clean, in a quiet neighborhood and perfect for our needs. Communication with the host was great. We look forward to staying here again in the future."

Diana M.

The price is €438

€438

includes taxes & fees

28 Nov - 29 Nov

Lakefront Property with Scenic View - All Seasons!

A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

A hotel room with two single beds, a small table, a chair, a nightstand with a lamp, and a window with curtains.

A modern living room with two sofas, a glass coffee table, and a decorative cake.

A wooden desk with a lamp, a coffee machine, and a trash bag.

18. Cozy 2-Bedroom Springfield Home 1.5 Baths

Cozy 2-Bedroom Springfield Home 1.5 Baths

Six Corners

The price is €227

€227

includes taxes & fees

29 Oct - 30 Oct

Cozy 2-Bedroom Springfield Home 1.5 Baths

A modern kitchen with blue cabinets, a central island, and a dining area with a glass table and chairs.

A bedroom with a bed, a nightstand, a lamp, a window with curtains, a television, and a bathroom door.

A living room with a TV, leather sofas, a coffee table, and a small side table.

An outdoor patio with wicker furniture, a glass-top table, and a barbecue grill.

19. Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville River Escape / Fall Foliage, Deck & Yard

Collinsville

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"This was a great weekend away in CT! The house was comfortable and clean. Very cozy setup and good communication with the host. The weather wasn’t amazing but we still enjoyed our stay for the weekend."

Brandon R.

The price is €190

€190

includes taxes & fees

4 Nov - 5 Nov

Collinsville River Escape / Fall Foliage, Deck & Yard

A modern living room with a sofa, a coffee table, and a red patterned rug.

A bedroom with a bed, a chair, a standing fan, and a mirror.

A narrow street flanked by two-story houses with a garage and a small tree.

A dining area with a glass table, grey chairs, and a vase of white flowers. There is a green upholstered chair, a chandelier, and a painting of a rose on the wall.

20. Cozy & Spacious Entire Home in Springfield

Cozy & Spacious Entire Home in Springfield

Forest Park

9.6 out of 10, Exceptional, (53 reviews)

9.6/10

Exceptional

(53 reviews)

"House was super clean, coffee was a nice surprise. Comfy beds, quiet street. Super close to the Big E. Thanks Rose!"

Brian

The price is €315

€315

includes taxes & fees

29 Oct - 30 Oct

Cozy & Spacious Entire Home in Springfield

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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