Westport, CT Vacation Homes from AED 559

Westport Vacation Homes
Connecticut
United States of America
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A calm river reflecting buildings and trees, with a clear sky above.

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Our top choices for Westport vacation homes

A glass-top table with ornate metal legs, a decorative bird figurine, and a candle holder on a textured rug.

A bedroom with a bed, a nightstand, a lamp, a mirror, a window with curtains, and a framed picture on the wall.

A kitchen with white cabinets, a stainless steel stove, a microwave, and a toaster.

A bathroom with a toilet, a sink, a mirror, and a shower curtain.

1. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature

Cranbury

The price is AED 859

AED 859

AED 1,580 total

includes taxes & fees

13 Oct - 14 Oct

Gilded Age Luxury Surrounded by Nature

A modern living room with a fireplace, a television, and a dining area with chairs and a table.

A modern living room with a white sectional sofa, a white armchair, a woven coffee table, and a potted plant.

A wooden deck with a hanging chair and a barbecue grill.

A bedroom with a white bed, two bedside tables, a chandelier, and two windows.

2. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Historic District

10.0 out of 10, Exceptional, (15 reviews)

10/10

Exceptional

(15 reviews)

"The property was very clean, host was excellent. The location is near restaurants, transportation, and grocery stores. Nice place to spend time with friends and family."

Melissa H.

The price is AED 1,054

AED 1,054

AED 2,499 total

includes taxes & fees

9 Nov - 10 Nov

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

A beach with people sunbathing and walking along the shore, a pier with a covered area, and buildings in the background.

A staircase with white balusters, a wicker chair, a lamp, and a television mounted on the wall.

A wooden chessboard on a round table with a checkered pattern, set against a backdrop of a living room with a sofa and a small side table.

A red barn with a sign that reads "Jones Winery."

3. Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Fairfield

10.0 out of 10, Exceptional, (41 reviews)

10/10

Exceptional

(41 reviews)

"Great accommodations and perfect location for us. "

Kim G.

The price is AED 790

AED 790

AED 2,123 total

includes taxes & fees

3 Nov - 4 Nov

Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

A modern living room with a grey sofa, a glass coffee table, and large windows offering views of the street.

A room with two beds, a radiator, and a window with blinds.

A house with a stone facade, a porch with steps, and a wooden ceiling.

A spacious living room with a large window, a ceiling fan, a grey sofa, and a coffee table.

4. Centric property close to all the great things in the city

Centric property close to all the great things in the city

Brooklawn - St. Vincent

6.6 out of 10, (17 reviews)

6.6/10

(17 reviews)

"This rental was great accommodation"

Alma B.

The price is AED 579

AED 579

AED 976 total

includes taxes & fees

13 Oct - 14 Oct

Centric property close to all the great things in the city

A modern kitchen with white cabinets, a central island with bar stools, a microwave, and a dishwasher.

A living room with a fireplace, a television, a large window, and two sofas.

A dining area with a wooden table and chairs, a white bench, and a window with a view of a brick building.

A two-story house with a front porch, a brick pathway leading to the door, and a small garden with flowers.

5. Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Fairfield

10.0 out of 10, Exceptional, (19 reviews)

10/10

Exceptional

(19 reviews)

"Place was very clean . Communication between owner and us was excellent."

gail s.

The price is AED 863

AED 863

AED 2,222 total

includes taxes & fees

15 Oct - 16 Oct

Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

A kitchen with wooden cabinets, a stainless steel refrigerator, a dining table, and a sofa.

A bedroom with a bed, a wooden nightstand, a door, and a mirror.

A bedroom with a wooden bed, a dresser, a mirror, and a ceiling light.

A kitchen with wooden cabinets, a marble countertop, a gas stove, a microwave, and a stainless steel refrigerator.

6. Elite room stay

Elite room stay

Bridgeport

The price is AED 760

AED 760

AED 1,256 total

includes taxes & fees

13 Oct - 14 Oct

Elite room stay

A swimming pool at night with blue lighting.

A kitchen area with a black refrigerator, a blue microwave, a coffee maker, and a small table with cereal boxes and a glass.

A two-story house with a front porch, a small front yard, and a solar panel on the roof.

A grey sofa against a brick wall, a bed with white bedding, and a tiled floor with a geometric pattern.

7. Business or Weekend escape

Business or Weekend escape

Stratford

9.2 out of 10, Wonderful, (60 reviews)

9.2/10

Wonderful

(60 reviews)

"Definitely clean - good place for an overnight stay."

Kimberly

The price is AED 331

AED 331

AED 559 total

includes taxes & fees

18 Oct - 19 Oct

Business or Weekend escape

A white room with a round table, two benches, and a window with a view of houses.

A modern kitchen with white cabinetry, stainless steel appliances, and a grey tiled floor.

A four-poster bed with a white bedspread, a wooden nightstand with a lamp, a wicker chair, and a white desk with a lamp.

A sandy beach path leading to a bench, with a calm body of water and boats in the distance.

8. Stay at Black Rock Harbor

Stay at Black Rock Harbor

Black Rock Historic District

10.0 out of 10, Exceptional, (29 reviews)

10/10

Exceptional

(29 reviews)

"This house was perfect for our family. Will definitely use again when we're visiting family in the area."

Laura L.

The price is AED 1,565

AED 1,565

AED 3,269 total

includes taxes & fees

1 Nov - 2 Nov

Stay at Black Rock Harbor

A modern kitchen with white cabinets, stainless steel appliances, a wooden island, and a painting on the wall.

A covered outdoor seating area with wicker sofas, a fire pit, and string lights.

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

A modern hotel room with a bed, a desk, a chair, a television, and a door leading to a balcony.

9. Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

Tunxis Hill

9.4 out of 10, Exceptional, (20 reviews)

9.4/10

Exceptional

(20 reviews)

"The house is very clean and spacious! Great location for what my party needed. The host is incredibly responsive and very helpful. Overall this was a fantastic stay and would recommend. "

Emily K.

The price is AED 1,267

AED 1,267

AED 2,796 total

includes taxes & fees

14 Oct - 15 Oct

Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

A modern kitchen with white cabinets, a marble island, and black bar stools.

A round wooden coffee table with a book and two vases of flowers.

A spacious living room with a sofa, two armchairs, a coffee table, and a fireplace.

A modern kitchen with white cabinetry, a marble countertop, and a stainless steel refrigerator.

10. Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit

West Norwalk

9.4 out of 10, Exceptional, (3 reviews)

9.4/10

Exceptional

(3 reviews)

"We had a wonderful stay."

Linda S.

The price is AED 1,392

AED 1,392

AED 2,950 total

includes taxes & fees

28 Oct - 29 Oct

Spacious Retreat with Game Room and Fire Pit

A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

A modern kitchen with wooden cabinets, stainless steel appliances, and a central island with stools.

A bedroom with a bed, two nightstands, a window with blinds, and two framed pictures on the wall.

A living room with a grey sectional sofa, a coffee table with decorative items, a white armchair, and a window with blinds.

11. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Waterside

10.0 out of 10, Exceptional, (21 reviews)

10/10

Exceptional

(21 reviews)

"Very nice location, easy check in and check out. Also very comfortable."

Leslie S.

The price is AED 579

AED 579

AED 1,216 total

includes taxes & fees

13 Oct - 14 Oct

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

A marina with boats docked, a Ferris wheel in the background, and a wooden pier with a sign.

A modern dining area with a glass table, grey upholstered chairs, and a view of the kitchen in the background.

12. 5BR Beach Home | Walk to Cove Beach + Private Yard

5BR Beach Home | Walk to Cove Beach + Private Yard

Cove - East Side - Shippan

9.8 out of 10, Exceptional, (26 reviews)

9.8/10

Exceptional

(26 reviews)

"The house was perfect! Plenty of bedding and the kitchen was well appointed. We were there for my fathers memorial and the living room provided a great space for us to connect and talk together. "

Maury A.

The price is AED 999

AED 999

AED 2,570 total

includes taxes & fees

14 Oct - 15 Oct

5BR Beach Home | Walk to Cove Beach + Private Yard

A modern living room with a fireplace, a flat-screen TV, and a decorative tray with snacks.

A dining area with a long table, blue upholstered chairs, a bench, and a blue cabinet with a pot on top.

A modern kitchen with white cabinetry, stainless steel appliances, and a large window with a view.

A backyard with a wooden fence, a fire pit, and three Adirondack chairs.

13. 4 Mi to Beach & Dtwn! Charming Fairfield Home

4 Mi to Beach & Dtwn! Charming Fairfield Home

Tunxis Hill

10.0 out of 10, Exceptional, (1 review)

10/10

Exceptional

(1 review)

"Beautiful home! Host was super responsive to questions. The entire house was super clean and welcoming. The bed was comfortable and smelled fresh. There was a personalized welcome sign that was a nice touch and some (much needed) snacks after our almost 3 hour drive. Expectations were well within reason and easily manageable. I would 100% rent again."

Raelyn O.

The price is AED 1,910

AED 1,910

AED 3,391 total

includes taxes & fees

13 Oct - 14 Oct

4 Mi to Beach & Dtwn! Charming Fairfield Home

A room with large windows overlooking a lake and greenery.

A modern building with a metal facade and a traditional house with a sloped roof.

A two-story house with a front yard, surrounded by trees and a clear blue sky.

14. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich

9.8 out of 10, Exceptional, (45 reviews)

9.8/10

Exceptional

(45 reviews)

"Nice stay"

Christopher J.

The price is AED 628

AED 628

AED 1,281 total

includes taxes & fees

14 Oct - 15 Oct

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

A modern kitchen with granite countertops, a dining area with black chairs, a living room with a sofa and a coffee table, and a large window with a view.

A modern living room with a sofa, ottoman, coffee table, and chairs. There is a staircase leading to a kitchen and dining area.

A spacious living room with a large window, a sofa set, a coffee table, and a view of a body of water.

A marina with boats docked, wooden piers, and modern buildings in the background.

15. 5BR Beach House, Water Views, Steps to Beach, Backyard

5BR Beach House, Water Views, Steps to Beach, Backyard

Cove - East Side - Shippan

9.4 out of 10, Exceptional, (31 reviews)

9.4/10

Exceptional

(31 reviews)

"The property was amazing. The house was clean, beautiful, and well equipped. Plenty of space yet still cozy. Host was very communicative and gracious, had a pleasant experience and will definitely be back!"

Maxx V.

The price is AED 1,756

AED 1,756

AED 3,507 total

includes taxes & fees

14 Oct - 15 Oct

5BR Beach House, Water Views, Steps to Beach, Backyard

A two-story house with a porch, stone steps, and a variety of plants.

A wooden staircase with a chandelier, leading to a room with a large window and a painting on the wall.

A two-story house with a gabled roof, a front porch, and a stone foundation.

A living room with a fireplace, wooden beams, a sofa, and a patterned armchair.

16. Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

North End

8.8 out of 10, Excellent, (10 reviews)

8.8/10

Excellent

(10 reviews)

"Plenty of bedrooms and space for the family. Very prompt communication with host."

David K.

The price is AED 2,420

AED 2,420

AED 4,790 total

includes taxes & fees

20 Oct - 21 Oct

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

A living room with a sofa set, a coffee table, and a television on a stand.

A spacious living room with a wooden floor, a beige sofa set, a coffee table, and a side table with a lamp.

A dining room with a wooden table and chairs, white curtains, and a vase on a side table.

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

17. Spacious Stamford Home | Family, Work, Parking

Spacious Stamford Home | Family, Work, Parking

Cove - East Side - Shippan

8.6 out of 10, Excellent, (9 reviews)

8.6/10

Excellent

(9 reviews)

"the home was nice clean if in the area I would stay here again"

james w.

The price is AED 1,050

AED 1,050

AED 2,108 total

includes taxes & fees

13 Oct - 14 Oct

Spacious Stamford Home | Family, Work, Parking

A two-story house with a blue exterior, a front porch, and a driveway leading to the entrance.

A spacious dining area with a large wooden table and black chairs, white walls, and a ceiling with exposed beams.

18. Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5.0 star property

North End

The price is AED 3,595

AED 3,595

AED 5,420 total

includes taxes & fees

12 Nov - 13 Nov

Beechmont - Perfect for Family Retreat!

A bedroom with a bed, bedside lamp, curtains, a hanging light fixture, and framed artwork on the wall.

A spacious kitchen with a central island, modern lighting, and a view to the outdoors.

A spacious living area with a sofa, ottoman, and a foosball table.

19. 5BR Beach House, Game Room + Huge Backyard

5BR Beach House, Game Room + Huge Backyard

Cove - East Side - Shippan

10.0 out of 10, Exceptional, (26 reviews)

10/10

Exceptional

(26 reviews)

"Very spacious and nicely decorated"

Linda M.

The price is AED 1,910

AED 1,910

AED 3,921 total

includes taxes & fees

14 Oct - 15 Oct

5BR Beach House, Game Room + Huge Backyard

A modern living room with a white sofa, a glass coffee table, and a piano.

A kitchen counter with a bottle of olive oil, a utensil holder with 'What's Cookin?' text, a knife block, and a kettle.

A living room with two white sofas, a glass coffee table, a fireplace, and a flat-screen TV mounted above it.

A black barbecue grill with a red gas canister, positioned in front of a brick house with a green door and white shutters.

20. Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

West Side

9.4 out of 10, Exceptional, (8 reviews)

9.4/10

Exceptional

(8 reviews)

"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."

Dave J.

The price is AED 1,355

AED 1,355

AED 2,545 total

includes taxes & fees

28 Oct - 29 Oct

Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

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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Top Westport Hotel Reviews

Comfort Inn & Suites Danbury-Bethel

8/10 Good

"Easy access"

Constance 3-night trip

Posted 10 hours ago

Comfort Inn & Suites Danbury-Bethel

J House Greenwich

8/10 Good

"THE LOBBY STAFF WAS CORDIAL, THE VALETS WERE VERY ACCOMODATING. THE ROOM WAS NOT AS PRISTINE CLEAN AS OUR FIRST VISIT, AND THE ROOM ACTUALLY HAD A BIT MORE WEAR AND TEAR. THE DRAPES WERE NOT WORKING EASILY AND THE BATHROOM DOOR DID NOT CLOSE ALL THE WAY."

Marianne 1-night trip

Posted 11 hours ago

J House Greenwich

Hyatt Regency Greenwich

10/10 Excellent

"EVEN THOUGH PROPERTY WAS LARGE, THE SERVICE WAS VERY PERSONAL WHEN AT THE LOBBY AND BAR. /IT WAS VERY DIFFICULT TO ORDER ROOM SERVICE. BUT WHEN WE GOT IT IT WAS GOOD"

Marianne 2-night trip

Posted 11 hours ago

Hyatt Regency Greenwich

Motel 6 Milford, CT

10/10 Excellent

"Great room with reasonable price"

Sanh 1-night trip

Posted 17 hours ago

Motel 6 Milford, CT

Red Carpet Inn

8/10 Good

"Good price compared to other hotels in the area. Friendly staff."

William 1-night trip

Posted 1 day ago

Red Carpet Inn

The Armon Stamford Hotel & Conference

10/10 Excellent

"Great stay, clean and warm"

Claudson 1-night trip

Posted 2 days ago

The Armon Stamford Hotel & Conference

Best Western Danbury/Bethel

8/10 Good

"The room was efficient as expected. The room was clean and neat. TV was interesting to say the least to use, maybe put out some directions. Honestly, a good stay and really no major complaint."

Jim 1-night trip

Posted 2 days ago

Best Western Danbury/Bethel

Search Vacation Homes in Westport

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Westport vacation homes

1. Gilded Age Luxury Surrounded by Nature

2. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

3. Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

4. Centric property close to all the great things in the city

5. Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

6. Elite room stay

7. Business or Weekend escape

8. Stay at Black Rock Harbor

9. Grand Fairfield Getaway- 5BR Fam-Friendly near I95&Shops - Spacious&Gracious

10. Spacious Retreat with Game Room and Fire Pit

11. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

12. 5BR Beach Home | Walk to Cove Beach + Private Yard

13. 4 Mi to Beach & Dtwn! Charming Fairfield Home

14. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

15. 5BR Beach House, Water Views, Steps to Beach, Backyard

16. Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

17. Spacious Stamford Home | Family, Work, Parking

18. Beechmont - Perfect for Family Retreat!

19. 5BR Beach House, Game Room + Huge Backyard

20. Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

Find vacation rentals that suit your style

Top Westport Hotel Reviews

Comfort Inn & Suites Danbury-Bethel