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Old Greenwich Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Old Greenwich vacation rentals

The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

1. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.2 out of 10, (198 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is ￥21,380
￥24,586 total
includes taxes & fees
Oct 25 - Oct 26
Stamford Suites
A house with a porch, a white door, and a window with blinds.

2. 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)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is ￥35,147
￥72,972 total
includes taxes & fees
Oct 26 - Oct 27
Gem by the water+ firepit and all fenced backyard
A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

3. Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
The price is ￥22,569
￥64,980 total
includes taxes & fees
Oct 25 - Oct 26
Modern Luxe 1BR Apt in Downtown Stamford
A modern living room with a sofa, a coffee table, and a bar stool.

4. Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is ￥22,569
￥49,150 total
includes taxes & fees
Oct 26 - Oct 27
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Interior

5. Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!

Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
Downtown Stamford
10.0 out of 10, Exceptional, (3 reviews)
"Had a lovely stay. Close to the train station and close to things in Stamford. Lovely space and owner was super helpful!"
United States
Marisa C.
The price is ￥23,510
￥42,396 total
includes taxes & fees
Nov 3 - Nov 4
Centrally-located Downtown Gem w/ free parking & Wi-Fi - convenient to NYC!
An outdoor seating area with tables and chairs, surrounded by planters with flowers, and a modern building in the background.

6. Seabreeze at the beach west beach Stamford ct.

Seabreeze at the beach west beach Stamford ct.
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (18 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is ￥37,649
￥94,514 total
includes taxes & fees
Nov 15 - Nov 16
Seabreeze at the beach west beach Stamford ct.
A modern living room with a white sofa, a glass coffee table, and a piano.

7. 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)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
The price is ￥51,878
￥100,958 total
includes taxes & fees
Oct 28 - Oct 29
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard
A modern kitchen with white cabinets, a dining area with wooden chairs, a large window, and a view of the city.

8. DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (115 reviews)
"I was there 4 times, excellent location, good rooms and nice people"
United States
slava
The price is ￥27,810
￥41,542 total
includes taxes & fees
Oct 29 - Oct 30
DUNE Fairfield Beach
A modern kitchen with white cabinets, a stainless steel refrigerator, a microwave, an oven, and a sink. There are two bar stools at the counter.

9. Modern Luxury 1BR Stamford Getaway

Modern Luxury 1BR Stamford Getaway
Downtown Stamford
8.0 out of 10, Very good, (2 reviews)
"The apartment is located in the hub bub of Stamford, a nice area very populated even in the evening where it feels safe. Apartment had all amenities that I needed. The host provided extra touches like a Keurig coffee pot stocked with Keurig cups and sugar. A washing machine and dryer were a plus as I like to pack only clean clothes. Bed was super comfortable. Modern design has a Zen vibe, great to decompress after travel. TV offered free movies that didn’t require my own subscription which...
United States
Debbie N.
The price is ￥31,189
￥56,242 total
includes taxes & fees
Oct 28 - Oct 29
Modern Luxury 1BR Stamford Getaway
A dock with kayaks and a canoe, surrounded by trees and a calm lake.

10. 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)
"Nice stay"
United States
Christopher J.
The price is ￥26,096
￥53,364 total
includes taxes & fees
Oct 25 - Oct 26
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
A modern kitchen with a central island, pendant lights, and built-in shelves.

11. Stylish Home and Cozy200

Stylish Home and Cozy200
Downtown Stamford
The price is ￥34,668
￥51,673 total
includes taxes & fees
Nov 3 - Nov 4
Stylish Home and Cozy200
Open concept kitchen

12. 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)
"Very spacious and nicely decorated"
United States
Linda M.
The price is ￥73,729
￥156,633 total
includes taxes & fees
Oct 25 - Oct 26
5BR Beach House, Game Room + Huge Backyard
A modern living room with a dark wooden panel wall, a framed picture of flowers, a chessboard, a vintage radio, and a potted plant.

13. Solara – Luxury 1BR Downtown

Solara – Luxury 1BR Downtown
Downtown Stamford
The price is ￥32,958
￥66,610 total
includes taxes & fees
Oct 27 - Oct 28
Solara – Luxury 1BR Downtown
A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a central island with stools.

14. 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)
"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. "
United States
Maury A.
The price is ￥120,476
￥205,250 total
includes taxes & fees
Nov 21 - Nov 22
5BR Beach Home | Walk to Cove Beach + Private Yard
A modern apartment with a dining area, kitchen, and living space.

15. Luxurious 3BR/2BA Modern Haven Downtown Stamford

Luxurious 3BR/2BA Modern Haven Downtown Stamford
Downtown Stamford
10.0 out of 10, Exceptional, (9 reviews)
"Great location with comfy beds and plenty of space."
United States
Nick D.
Luxurious 3BR/2BA Modern Haven Downtown Stamford
A living room with a sofa, armchair, ottoman, and coffee table.

16. Spacious Stamford Home | Family, Work, Parking

Spacious Stamford Home | Family, Work, Parking
Cove - East Side - Shippan
8.6 out of 10, Excellent, (9 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is ￥37,302
￥80,199 total
includes taxes & fees
Oct 26 - Oct 27
Spacious Stamford Home | Family, Work, Parking
A living room with a sofa, a glass coffee table, a fireplace, and a TV mounted above it.

17. Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (34 reviews)
"Exactly as described, comfy and close to the Capital and restaurants. We would definitely stay here again.Directions and parking instructions were very clear and helpful."
United States
Sarah W.
The price is ￥34,481
￥65,252 total
includes taxes & fees
Oct 27 - Oct 28
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
A modern kitchen with a central island, pendant lights, and built-in shelves.

18. Stylish Home With Free ParkingZA

Stylish Home With Free ParkingZA
Glenbrook-Belltown
The price is ￥34,637
￥51,313 total
includes taxes & fees
Nov 18 - Nov 19
Stylish Home With Free ParkingZA
A wooden staircase leading to a gazebo in a forested area with a metal railing.

19. Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich

Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Greenwich
8.6 out of 10, Excellent, (7 reviews)
"This was a warm and inviting space. CC even offered me breakfast. I was a single woman in for a class reunion and had be somewhere on Sat and Sunday mornings. It was lovely coming back to relax and read. The space is small perfect for a couple with a young person. The patio over looks the river. The house is on a cul-de-sac perfect for strolling around the neighborhood. Very quiet and safe. Well lit path at night to the back, private entrance. Small fridge but holds a lot. Microwave, kurgurg...
United States
Kathleen W.
The price is ￥35,264
￥46,878 total
includes taxes & fees
Oct 25 - Oct 26
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
A rustic cabin surrounded by lush greenery and a stone pathway leading to it.

20. Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC

Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
Greenwich
10.0 out of 10, Exceptional, (13 reviews)
"Beautiful and restful"
United States
Lisa H.
The price is ￥126,246
￥251,329 total
includes taxes & fees
Oct 25 - Oct 26
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
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

Ardsley Acres Hotel Westchester

Ardsley Acres Hotel Westchester

10/10 Excellent
"Clean and convenient. Great overnight stop."
Sean 1-night trip
Posted 9 hours ago
Ardsley Acres Hotel Westchester

Find out more about Old Greenwich

Search for holiday rentals in Old Greenwich on Expedia! You can easily find your home rentals, villas, holiday apartments in Old Greenwich using one of the methods below:

  • View our selection of featured holiday rentals in Old Greenwich
  • Use the map to find apartments and other holiday homes in the Old Greenwich neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Old Greenwich while they last

Look no further and take a look at our great range of rental properties in Old Greenwich!

Frequently asked questions

Can I find vacation rentals in Old Greenwich?

Yes, we offer vacation rentals close to well known points of interest in Old Greenwich, or you can go with a more remote option if you want a relaxing place to stay. Visitors like the top-notch restaurants and shops in Old Greenwich. Make sure you have time to check out the beaches and cafes during your trip.

What are some of the best vacation rentals in Old Greenwich?

Modern Luxury Home w GameRoom & Parking: Located near Old Greenwich, this vacation home rental is situated near the airport and has a rooftop terrace and free WiFi to help you feel content during your stay. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Old Greenwich?

Expedia has 13 vacation rentals for your stay in Old Greenwich.

What can I see and do in Old Greenwich?

Greenwich Point Park and Rosa Hartman Park are a couple of lovely local spots to get outside and enjoy nature. Commerce Park and Dundee Woods are other places to visit while you're in town.

What are vacation rentals like in Old Greenwich?

Vacation rentals are privately owned accommodations you can reserve for a short or long stay in Old Greenwich. Vacation rentals provide amenities like WiFi and washers and dryers so you'll have all the conveniences of home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from shared hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for a family trip.