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Our top choices for Darien holiday homes

An outdoor seating area with a round table, a chair, and a hanging light fixture.

A residential property with a front yard, a stone staircase leading to the entrance, and a gated driveway.

A living room with two sofas, a coffee table, and a radiator.

1. Gem by the water+ firepit and all fenced backyard

Gem by the water+ firepit and all fenced backyard

Waterside

10.0 out of 10, Exceptional, (21 reviews)

10/10

Exceptional

(21 reviews)

"Property was exactly what we needed for our stay"

Christopher E.

The price is €390

€390

includes taxes & fees

30 Nov - 1 Dec

Gem by the water+ firepit and all fenced backyard

A living room with a sofa, armchair, ottoman, and coffee table.

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

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

2. Stamford Home | Family, Work and Plenty of Parking

Stamford Home | Family, Work and Plenty of 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 €452

€452

includes taxes & fees

3 Nov - 4 Nov

Stamford Home | Family, Work and Plenty of Parking

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

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

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

A spacious living room with a leather sofa, white armchairs, and a staircase leading to another level.

3. 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 €694

€694

includes taxes & fees

18 Nov - 19 Nov

Spacious Retreat with Game Room and Fire Pit

A dock with kayaks and a canoe, surrounded by trees and a calm lake.

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

A room with large windows overlooking a lake and greenery.

A bedroom with a large window, a bed, and a flat-screen TV mounted on the wall.

4. 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, (46 reviews)

9.8/10

Exceptional

(46 reviews)

"Nice stay"

Christopher J.

The price is €402

€402

includes taxes & fees

30 Nov - 1 Dec

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

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 modern kitchen with white cabinetry, stainless steel appliances, and a black granite countertop.

5. 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.

5BR Beach House, Game Room + Huge Backyard

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

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.

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

6. Spacious 3BR Townhome | Garage + Near Downtown

Spacious 3BR Townhome | Garage + Near Downtown

West Side

9.2 out of 10, Wonderful, (9 reviews)

9.2/10

Wonderful

(9 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 €530

€530

includes taxes & fees

2 Nov - 3 Nov

Spacious 3BR Townhome | Garage + Near Downtown

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

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

A residential backyard with a stone patio, outdoor furniture, a wooden fence, and a view of a lake.

7. 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, (32 reviews)

9.4/10

Exceptional

(32 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 €953

€953

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

A modern living room with a sectional sofa, a coffee table, and a large window with curtains.

8. 5BR Beach Home | Walk to Cove Beach + Private Yard

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

Cove - East Side - Shippan

9.6 out of 10, Exceptional, (27 reviews)

9.6/10

Exceptional

(27 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.

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

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 dining area with a table and chairs, a vase with flowers, and a fireplace in the background.

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

9. 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 €604

€604

includes taxes & fees

9 Nov - 10 Nov

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

A two-story house with a front porch, a chimney, and a well-maintained garden with a stone pathway leading to the entrance.

A modern kitchen with white cabinetry, a stainless steel refrigerator, a dishwasher, and a microwave.

A bedroom with a wooden staircase, two beds, a nightstand, and a wall-mounted lamp.

10. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature

Cranbury

Gilded Age Luxury Surrounded by Nature

A square fire pit with flames, surrounded by a wooden deck, set against a backdrop of a lake and trees under a clear sky.

A dining area with a table and chairs, a painting on the wall, and a view through large windows.

A modern living room with a large gray sectional sofa, a glass coffee table, and a view of a snowy landscape through large windows.

A modern kitchen with white cabinetry, a central island, stainless steel appliances, pendant lighting, and a large window offering a view of the outdoors.

11. Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views

Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views

Greenwich

10.0 out of 10, Exceptional, (2 reviews)

10/10

Exceptional

(2 reviews)

"Great location on the lake which the kids loved. The hosts were very friendly and easy to communicate with. The addition of the outdoor grill was a big plus and we enjoyed many afternoons out on the deck. We would stay again."

Nathan R.

The price is €2,152

€2,152

includes taxes & fees

1 Nov - 2 Nov

Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views

A modern kitchen with a marble island, bar stools, and a built-in oven.

A modern kitchen with a marble countertop, a built-in oven, and a sliding door leading to a dining area.

A patio area with a wooden table and blue upholstered chairs, a white fence, and a tree in the background.

A building with a white door, black trim, and a stone-paved entrance.

12. Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Huntington

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"Wonderful time for stay."

Logan M.

The price is €372

€372

includes taxes & fees

29 Nov - 30 Nov

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

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

A modern living room with a large sofa, a fireplace, and a television.

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

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

13. 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 €496

€496

includes taxes & fees

3 Nov - 4 Nov

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

A swimming pool at night with blue lighting.

A room with a bed, a sofa, a dining table with chairs, and a small desk with a keyboard and mouse.

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.

14. 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 €140

€140

includes taxes & fees

9 Nov - 10 Nov

Business or Weekend escape

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 residential street with a house featuring a stone pathway, a white railing, and a clear sky.

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

15. 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

6.8 out of 10, (18 reviews)

6.8/10

(18 reviews)

"This rental was great accommodation"

Alma B.

The price is €261

€261

includes taxes & fees

30 Nov - 1 Dec

Centric property close to all the great things in the city

A lakeside view with boats docked, surrounded by autumn-colored trees and houses.

A dining area with a table set for four, a coffee machine, and a window with a view of trees.

A spacious living room with a ceiling fan, large windows, and a door leading outside.

A cozy room with a dining table, two chairs, and a view through large windows.

16. Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor

10.0 out of 10, Exceptional, (88 reviews)

10/10

Exceptional

(88 reviews)

"Comfortable beds and close to good food"

Stacey S.

The price is €579

€579

includes taxes & fees

8 Nov - 9 Nov

Captain's Cottage - Cold Spring Harbor Water Views

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

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

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

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

17. Elite room stay

Elite room stay

Bridgeport

The price is €312

€312

includes taxes & fees

1 Nov - 2 Nov

Elite room stay

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

A white two-story house with a front porch, a number '65' on the door, and a mailbox.

18. Stay at Black Rock Harbor

Stay at Black Rock Harbor

Black Rock Historic District

10.0 out of 10, Exceptional, (30 reviews)

10/10

Exceptional

(30 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 €775

€775

includes taxes & fees

1 Nov - 2 Nov

Stay at Black Rock Harbor

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

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

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

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

19. 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)

"Beautiful home, clean and exactly as described.We loved our stay and plan on returning.The host was wonderful to work with.An overall excellent experience."

Tara C.

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

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

A modern kitchen with a wooden island, white cabinetry, and a large painting above the island.

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

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

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

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

Tunxis Hill

9.6 out of 10, Exceptional, (21 reviews)

9.6/10

Exceptional

(21 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 €700

€700

includes taxes & fees

4 Nov - 5 Nov

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

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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