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Old Greenwich Vacation Rentals

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

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, (173 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is ￥24,454
￥28,123 total
includes taxes & fees
Sep 20 - Sep 21
Stamford Suites
A round outdoor seating area with a teal cushion and patterned pillows, surrounded by greenery and a bamboo wall with string lights.

2. 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
9.8 out of 10, Exceptional, (19 reviews)
"Very nice location, easy check in and check out. Also very comfortable."
United States
Leslie S.
The price is ￥29,585
￥57,832 total
includes taxes & fees
Sep 15 - Sep 16
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
A kitchen counter with a bottle of olive oil, a utensil holder with 'What's Cookin?' text, a knife block, and a kettle.

3. 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)
"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 ￥57,911
￥107,381 total
includes taxes & fees
Sep 13 - Sep 14
Urban Oasis 45 min to NYC 2.5 Bath + Garage + Yard

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)
"Great stay!"
United States
Kyra S.
The price is ￥89,401
￥176,793 total
includes taxes & fees
Sep 16 - Sep 17
5BR Beach House, Game Room + Huge Backyard
A modern living room with a glass coffee table, black and gold chairs, and a striped area rug.

5. 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 ￥22,120
￥63,687 total
includes taxes & fees
Sep 13 - Sep 14
Modern Luxe 1BR Apt in Downtown Stamford
A rustic cabin surrounded by lush greenery and a stone pathway leading to it.

6. 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, (12 reviews)
"Beautiful and restful"
United States
Lisa H.
The price is ￥123,733
￥246,326 total
includes taxes & fees
Sep 13 - Sep 14
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
An outdoor seating area with tables and chairs, surrounded by planters with flowers, and a modern building in the background.

7. Seabreeze at the beach west beach Stamford ct.

Seabreeze at the beach west beach Stamford ct.
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (16 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is ￥35,945
￥86,191 total
includes taxes & fees
Sep 22 - Sep 23
Seabreeze at the beach west beach Stamford ct.
A campfire with a wooden table and benches by a lake.

8. 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, (42 reviews)
"Nice stay"
United States
Christopher J.
The price is ￥29,186
￥53,380 total
includes taxes & fees
Oct 4 - Oct 5
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
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
10.0 out of 10, Exceptional, (1 review)
"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 ￥30,568
￥55,430 total
includes taxes & fees
Sep 27 - Sep 28
Modern Luxury 1BR Stamford Getaway
A modern living room with a sofa, a coffee table, a TV, and a large window with a view of buildings.

10. Avora | Quiet Luxury | Downtown Stamford | 2BR/2BA

Avora | Quiet Luxury | Downtown Stamford | 2BR/2BA
Downtown Stamford
The price is ￥61,674
￥91,628 total
includes taxes & fees
Sep 27 - Sep 28
Avora | Quiet Luxury | Downtown Stamford | 2BR/2BA
A modern living room with a sofa, a coffee table, and a bar stool.

11. 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 ￥24,578
￥51,306 total
includes taxes & fees
Sep 28 - Sep 29
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A dining table set with blue bowls, gold cutlery, and yellow lemons.

12. Romantic Hide Out

Romantic Hide Out
Waterside
3.0 out of 10, (2 reviews)
"Check-in was at 3 PM and I was unable to reach the host until 11 PM that night to gain access to the property. They never sent anything in advance. It was the most miserable experience I have ever had."
United States
Cheryl H.
The price is ￥16,590
￥37,204 total
includes taxes & fees
Sep 14 - Sep 15
Romantic Hide Out
A living room with a sofa, a glass coffee table, a fireplace, and a TV mounted above it.

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

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (33 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 ￥33,794
￥60,613 total
includes taxes & fees
Sep 20 - Sep 21
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
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.

14. 5BR Beach House, Water Views, Game Room, Backyard

5BR Beach House, Water Views, Game Room, Backyard
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (31 reviews)
"House was a good location. Many fun outdoor activities."
United States
Heather G.
The price is ￥66,233
￥137,530 total
includes taxes & fees
Sep 21 - Sep 22
5BR Beach House, Water Views, Game Room, Backyard
A living room with a sofa set, a coffee table, and a television on a stand.

15. 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 ￥41,321
￥84,232 total
includes taxes & fees
Sep 13 - Sep 14
Spacious Stamford Home | Family, Work, Parking
A wooden staircase leading to a gazebo in a forested area with a metal railing.

16. 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
8.0 out of 10, Very Good, (5 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 ￥25,991
￥34,966 total
includes taxes & fees
Sep 25 - Sep 26
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
A square fire pit with flames, surrounded by a wooden deck, set against a backdrop of a lake and trees under a clear sky.

17. 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, (1 review)
"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."
United States
Nathan R.
The price is ￥298,464
￥465,046 total
includes taxes & fees
Sep 27 - Sep 28
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
A modern kitchen with a central island, pendant lights, and built-in shelves.

18. Stylish Home and Cozy

Stylish Home and Cozy
Downtown Stamford
The price is ￥73,733
￥100,845 total
includes taxes & fees
Sep 15 - Sep 16
Stylish Home and Cozy
A wooden gazebo with a tiled roof at the top of a stone staircase surrounded by trees.

19. 2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.5 star property
Greenwich
The price is ￥27,803
￥51,422 total
includes taxes & fees
Sep 30 - Oct 1
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
A hotel entrance with a covered walkway, a prominent tower, and a well-lit facade.

20. Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is ￥33,305
￥38,300 total
includes taxes & fees
Sep 15 - Sep 16
Guesthouse at Norwalk Inn
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

Hotel Nyack, a JdV by Hyatt Hotel

Hotel Nyack, a JdV by Hyatt Hotel

8/10 Good
"Clean room. Staff were friendly. Available parking spaces. Excellent stay only minor thing was that the AC vent was directly over the bed so the cold air blows right toward the bed. Other than that the stay was great."
Jasmine 1-night trip
Posted 4 hours ago
Hotel Nyack, a JdV by Hyatt Hotel

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:

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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.