Old Greenwich Holiday House Rentals from AU$195: Search Holiday Homes

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Our top choices for Old Greenwich holiday homes

A patio with outdoor furniture, a grill, and potted plants.

A bedroom with a bed, two nightstands, a window with shutters, and wall art.

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

A kitchen with wooden cabinets, a refrigerator, a stove, and a bar stool.

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)

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

Leslie S.

The price is AU$655

AU$655

includes taxes & fees

26 Oct - 27 Oct

Gem by the water+ firepit and all fenced 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.

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

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

West Side

9.2 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 AU$892

AU$892

includes taxes & fees

27 Oct - 28 Oct

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

A room with large windows overlooking a lake and greenery.

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.

3. 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 AU$518

AU$518

includes taxes & fees

25 Oct - 26 Oct

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

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

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

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

4. 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 AU$1,240

AU$1,240

includes taxes & fees

27 Oct - 28 Oct

5BR Beach House, Game Room + Huge Backyard

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

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

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

A neatly arranged bedroom with a bed, nightstands, a radiator, and a window with curtains.

5. 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 AU$727

AU$727

includes taxes & fees

26 Oct - 27 Oct

Spacious Stamford Home | Family, Work, Parking

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

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

6. 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 AU$1,785

AU$1,785

includes taxes & fees

19 Nov - 20 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 living room with a sectional sofa, a coffee table, and a large window with curtains.

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.

7. 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 AU$953

AU$953

includes taxes & fees

28 Oct - 29 Oct

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

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.

8. 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 AU$4,188

AU$4,188

includes taxes & fees

25 Oct - 26 Oct

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

A covered porch with wooden rocking chairs and a table, overlooking a body of water with boats and a bridge in the distance.

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

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

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

9. 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 AU$693

AU$693

includes taxes & fees

26 Oct - 27 Oct

Captain's Cottage - Cold Spring Harbor Water 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 modern, well-lit bedroom with a large bed, a washing machine, and a kitchen area with white cabinets and a countertop.

10. 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 AU$631

AU$631

includes taxes & fees

22 Oct - 23 Oct

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

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

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

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.

11. 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 AU$1,069

AU$1,069

includes taxes & fees

18 Nov - 19 Nov

Spacious Retreat with Game Room and Fire Pit

A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

A bedroom with a bed, a dresser, a vanity, and a television.

A casino floor with multiple blackjack tables and chairs.

A modern living room with a patterned wallpaper, a dark sofa with multiple cushions, a white fluffy rug, and a side table with a lamp.

12. Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Southeast Yonkers

7.8 out of 10, Good, (19 reviews)

7.8/10

Good

(19 reviews)

"Great location"

Jordan S.

The price is AU$195

AU$195

includes taxes & fees

27 Oct - 28 Oct

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

An outdoor patio with a fire pit, green chairs, and a table.

A modern living room with a grey sofa, a patterned rug, and a small side table.

A paved pathway curving through a grassy area with a car parked in the background.

A kitchen with wooden cabinets, a black stove, a wooden dining table with four chairs, a ceiling fan, and a wall clock.

13. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

New Rochelle

10.0 out of 10, Exceptional, (12 reviews)

10/10

Exceptional

(12 reviews)

"Host was very polite and helpful. Excellent condition VRBO."

Drew C.

The price is AU$495

AU$495

includes taxes & fees

27 Oct - 28 Oct

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

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

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

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

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

14. 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 AU$930

AU$930

includes taxes & fees

9 Nov - 10 Nov

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

A living room with a sofa, a coffee table, a wicker chair, a ceiling fan, and a large window with a view of a parked car outside.

A kitchenette with a microwave, a red popcorn vending machine, and a snack bar sign.

A modern kitchen with wooden cabinets, stainless steel appliances, and a glass shelving unit.

A bedroom with a bed, bedside tables, a chair, and a window.

15. Huntington Village 4BR Walkable Sleeps 8

Huntington Village 4BR Walkable Sleeps 8

Huntington

10.0 out of 10, Exceptional, (5 reviews)

10/10

Exceptional

(5 reviews)

"The house was in an ideal location! Unfortunately, there was a nor easterner so walking was not an option but on a lovely day, it would be a perfect house to stay in and explore Huntington! The bedrooms were ideal."

Susan

The price is AU$1,158

AU$1,158

includes taxes & fees

27 Oct - 28 Oct

Huntington Village 4BR Walkable Sleeps 8

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

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

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

16. Gilded Age Luxury Surrounded by Nature

Gilded Age Luxury Surrounded by Nature

Cranbury

The price is AU$799

AU$799

includes taxes & fees

22 Oct - 23 Oct

Gilded Age Luxury Surrounded by Nature

A modern outdoor patio with a seating area, a central table, and a large umbrella.

A modern kitchen with a large island, bar stools, and a view of the outdoors through large windows.

A modern interior with a sliding glass door leading to a garden, a white sofa with cushions, and a glass coffee table.

A serene park with a pond, a wooden bridge, and a gazebo.

17. Mansion in Greenwich with private lake and river

Mansion in Greenwich with private lake and river

Greenwich

9.8 out of 10, Exceptional, (6 reviews)

9.8/10

Exceptional

(6 reviews)

"Beautiful home. Exquisite decor and our kids enjoyed fishing right out back. Thoroughly enjoyed. "

J.J. O.

Mansion in Greenwich with private lake and river

A room with a wooden door, a small table with a vase, and a chair.

A dining area with a stone fireplace, a chandelier, and a view of the kitchen through a window.

A laundry room with a washing machine and dryer, a patterned floor, and an arched doorway leading to a hallway with a tiled floor and a door.

A modern kitchen with dark cabinetry, a stainless steel range hood, a sink, and a countertop with a bowl of lemons.

18. Spacious 3b/3b Mediterranean in White Plains

Spacious 3b/3b Mediterranean in White Plains

White Plains

9.4 out of 10, Exceptional, (18 reviews)

9.4/10

Exceptional

(18 reviews)

"This was a wonderful property. It was very charming and had everything we could need. Great neighborhood, lots of room very comfortable. We would definitely stay there again. Great host response!"

Nancy K.

The price is AU$1,232

AU$1,232

includes taxes & fees

22 Oct - 23 Oct

Spacious 3b/3b Mediterranean in White Plains

A modern kitchen with granite countertops, stainless steel appliances, and white cabinetry.

A dining area with a wooden table, chairs, and a chandelier. There is a leather sofa and a window with a view of trees.

A narrow pathway flanked by a wooden fence and a brick wall, leading to a small garden area with green shrubs and purple flowers.

A living room with a fireplace, a large TV, and a dining area.

19. Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village

Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village

Huntington

9.2 out of 10, Wonderful, (12 reviews)

9.2/10

Wonderful

(12 reviews)

"Great place to stay"

Michael D.

The price is AU$879

AU$879

includes taxes & fees

28 Oct - 29 Oct

Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village

A room with two beds, white curtains, a ceiling light, and a window with a view.

A modern living room with a flat-screen TV mounted on a white wall, wooden flooring, and a large abstract rug.

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

A modern living room with a white sectional sofa, a glass coffee table, and a grey armchair.

20. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

White Plains

2.0 out of 10, (1 review)

2.0/10

(1 review)

"This guy is a scammer, an hour before my checkin they finally sent me the "location" and claimed they needed more time to clean the property. Then at 5 pm and hour after they claimed their was a gas leak and I couldn't stay there. Only thing is the address they sent me wasn't real and I am convinced this listing is fake in and used to trick people into staying at their actual property in yonkers. DO NOT RENT FROM THEM!"

Ethan G.

The price is AU$1,162

AU$1,162

includes taxes & fees

22 Oct - 23 Oct

Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

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 Old Greenwich Hotel Reviews

Baymont by Wyndham White Plains - Elmsford

8/10 Good

"Good location great parking would return"

Edward 1-night trip

Posted less than an hour ago

Baymont by Wyndham White Plains - Elmsford

Royal Regency Hotel

8/10 Good

"The staff was very helpful and friendly"

Garfield 2-night trip

Posted 1 hour ago

Royal Regency Hotel

Hyatt Regency Greenwich

10/10 Excellent

"Beautiful hotel!! The front desk staff, bar and restaurant staff were all amazing, very friendly and very accommodating on all aspects. I highly recommend this hotel, it has the look and feel of a resort."

Cynthia 1-night trip

Posted 1 hour ago

Hyatt Regency Greenwich

Tarrytown House Estate

10/10 Excellent

"Everything was incredible and the grounds were beautiful! We only stayed one night but can’t wait to be back for a longer trip!"

Colleen 1-night trip

Posted 3 hours ago

Tarrytown House Estate

Hampton Inn White Plains/Tarrytown

8/10 Good

"Nice"

Makayla 1-night trip

Posted 4 hours ago

Hampton Inn White Plains/Tarrytown

Sonesta White Plains Downtown

10/10 Excellent

"What a surprise! I was looking for something close to Westchester airport (10 mins) and did not expect this to be as great as it was."

Nicole 1-night trip

Posted 6 hours ago

Sonesta White Plains Downtown

West Gate Inn Nyack

10/10 Excellent

"Breakfast is good."

Shiqian 1-night trip

Posted 2 days ago

West Gate Inn Nyack

Westchester Marriott

8/10 Good

"C"

Prashant 1-night trip

Posted 3 days ago

Westchester Marriott

Hotel Nyack, a JdV by Hyatt Hotel

8/10 Good

"Overall great place and would stay again. The beds are not as comfortable as I had hoped. We had a few issues with the room at check but the staff were great and super fast to resolve the issues"

Wade 2-night trip

Posted 4 days ago

Hotel Nyack, a JdV by Hyatt Hotel

Find out more about Old Greenwich

Old Greenwich Holiday Homes information

Number of reviews	327
Accommodation	235 Holiday Homes
Lowest Price	AU$195
Highest Price	AU$4,188

Explore a world of travel with Expedia

More ways to book

Book Holiday Homes in Old Greenwich on Expedia.com

Holiday Homes in Old Greenwich

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Old Greenwich holiday homes

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

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

3. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

4. 5BR Beach House, Game Room + Huge Backyard

5. Spacious Stamford Home | Family, Work, Parking

6. 5BR Beach House, Water Views, Steps to Beach, Backyard

7. 5BR Beach Home | Walk to Cove Beach + Private Yard

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

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

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

11. Spacious Retreat with Game Room and Fire Pit

12. Nice Cozy Room By Empire City Casino And Cross County Shopping Center

13. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

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

15. Huntington Village 4BR Walkable Sleeps 8

16. Gilded Age Luxury Surrounded by Nature

17. Mansion in Greenwich with private lake and river

18. Spacious 3b/3b Mediterranean in White Plains

19. Spacious 3BR Modern Family Retreat Near Oheka Castle and Huntington Village

20. Comfortable 3BR • Complimentary Parking • Minutes from NYC • Ideal for Groups

Find holiday rentals that suit your style

Top Old Greenwich Hotel Reviews

Baymont by Wyndham White Plains - Elmsford

Find out more about Old Greenwich

Old Greenwich Holiday Homes information

Explore a world of travel with Expedia