Lodging Image

Old Greenwich Vacation Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Old Greenwich vacation rentals

Exterior

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (145 reviews)
"Great location, friendly and helpful staff. Good value for money."
United States
ian
The price is ￥23,758
￥27,322 total
includes taxes & fees
Aug 3 - Aug 4
Stamford Suites
Property grounds

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, (17 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is ￥36,692
￥67,902 total
includes taxes & fees
Jul 30 - Jul 31
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Interior

Walkable Townhouse with Garage & Yard, 45 min to NYC!

Walkable Townhouse with Garage & Yard, 45 min to NYC!
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 ￥60,973
￥111,215 total
includes taxes & fees
Jul 30 - Jul 31
Walkable Townhouse with Garage & Yard, 45 min to NYC!
Smart TV

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 ￥26,197
￥71,550 total
includes taxes & fees
Aug 19 - Aug 20
Modern Luxe 1BR Apt in Downtown Stamford
Offices

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 ￥23,577
￥51,018 total
includes taxes & fees
Jul 30 - Jul 31
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Private kitchen

Modern Luxury 1BR Stamford Getaway

Modern Luxury 1BR Stamford Getaway
Downtown Stamford
10.0 out of 10, Exceptional, (1 review)
The price is ￥32,582
￥58,263 total
includes taxes & fees
Aug 13 - Aug 14
Modern Luxury 1BR Stamford Getaway
Dining

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 ￥19,598
￥42,350 total
includes taxes & fees
Aug 6 - Aug 7
Romantic Hide Out
TV

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 ￥36,021
￥67,603 total
includes taxes & fees
Aug 3 - Aug 4
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Apartment (1 Bedroom) | Interior

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 ￥27,834
￥52,739 total
includes taxes & fees
Aug 4 - Aug 5
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
TV, fireplace, foosball, offices

New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (25 reviews)
"Excellent home, met all expectations, and attentive staff"
United States
Steve G.
New Beach Home near Stamford Downtown/Shippan
Coffee/tea maker, fridge, microwave, oven

Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (26 reviews)
"Lovely place, great location, had absolutely everything we needed! Would absolutely stay here again. "
United States
Erin D.
The price is ￥66,638
￥142,863 total
includes taxes & fees
Aug 4 - Aug 5
Stylish Beach Home near Stamford Downtown/Beach
TV

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Spacious 3 Bd Home Pet Friendly, Parking and Laundry
Cove - East Side - Shippan
8.4 out of 10, Very Good, (7 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
The price is ￥29,078
￥70,443 total
includes taxes & fees
Jul 30 - Jul 31
Spacious 3 Bd Home Pet Friendly, Parking and Laundry
Standard Room, 1 King Bed, Main Building | Property entrance

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 ￥58,779
￥67,596 total
includes taxes & fees
Aug 4 - Aug 5
Guesthouse at Norwalk Inn
Coffee/tea maker, fridge, microwave, oven

Stylish Home With Free ParkingZA

Stylish Home With Free ParkingZA
Glenbrook-Belltown
The price is ￥38,640
￥55,652 total
includes taxes & fees
Jul 30 - Jul 31
Stylish Home With Free ParkingZA
Interior

Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach
Cove - East Side - Shippan
9.4 out of 10, Exceptional, (31 reviews)
"We loved this house! The view is gorgeous and it's close to everything we needed. The pool table was a fun bonus!"
United States
Laura M.
The price is ￥94,214
￥177,238 total
includes taxes & fees
Aug 26 - Aug 27
Waterview House Walking Distance from Cove Beach
Smart TV, offices

Comfort Meets Convenience Parking, Gym, near NYC

Comfort Meets Convenience Parking, Gym, near NYC
Downtown Stamford
The price is ￥49,119
￥84,272 total
includes taxes & fees
Aug 27 - Aug 28
Comfort Meets Convenience Parking, Gym, near NYC
Property grounds

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
7.6 out of 10, Good, (4 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 ￥27,703
￥36,942 total
includes taxes & fees
Aug 4 - Aug 5
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Coffee/tea maker, fridge, microwave, oven

Stylish Home and Cozy

Stylish Home and Cozy
Downtown Stamford
The price is ￥58,779
￥81,431 total
includes taxes & fees
Aug 2 - Aug 3
Stylish Home and Cozy
Property grounds

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, (7 reviews)
"This house is the perfect private getaway! Everything was just as described and the host was super helpful. Will definitely stay again. "
United States
Anna F.
The price is ￥88,709
￥207,376 total
includes taxes & fees
Aug 9 - Aug 10
Riverfront Cottage w/ Heated Pool, Hot Tub & Fireplace, 35 min to NYC
Villa, Garden View | Living area

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
4.0 out of 10, (1 review)
"After flying in with four of us from Los Angeles on a Red Eye, we had to drive around for 4-5 hours until we were able to check in at 4pm, however after hours of trying to get into the property with no answer on the contact number ,we finally were able to have the local property manager come out and say that the property overbooked and had no room for us. I spent over 2 hours on the phone getting the run around by Expedia with mixed stories of our accommodations. FINALLY with now the story is...
United States
Jorge
The price is ￥74,617
￥109,757 total
includes taxes & fees
Jul 30 - Jul 31
Luxury NYC Home Game Room Free Parking
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Old Greenwich Hotel Reviews

Hampton Inn & Suites Yonkers

Hampton Inn & Suites Yonkers

10/10 Excellent
"Loved it the only thing the pool was closed they should’ve emailed me about it or said something till i got there cause that was main goal"
Karen 1-night trip
Posted 1 hour ago
Hampton Inn & Suites Yonkers

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?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This vacation home rental near Old Greenwich is equipped with a garden, air-conditioning, and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop, and a microwave.

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.