Old Greenwich Vacation Rentals

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Check prices for these dates

In two weeks
Jun 5 - Jun 7
In two months
Jul 17 - Jul 19
In three months
Aug 14 - Aug 16
In four months
Sep 11 - Sep 13

Our top choices for Old Greenwich vacation rentals

Marina

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, (78 reviews)
"Location was perfect!"
United States
Linda J P.
The price is ￥48,416
￥96,484 total
includes taxes & fees
May 21 - May 22
Captain's Cottage - Cold Spring Harbor Water Views
Property grounds

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, (34 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is ￥27,145
￥50,900 total
includes taxes & fees
May 21 - May 22
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Classic Suite | Iron/ironing board, free WiFi, bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (88 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is ￥27,982
￥41,863 total
includes taxes & fees
May 26 - May 27
DUNE Fairfield Beach
Outdoor dining

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
Huntington
9.8 out of 10, Exceptional, (7 reviews)
"Host was very accommodating - lovely property!"
United States
Mary C.
The price is ￥23,017
￥36,273 total
includes taxes & fees
May 26 - May 27
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
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, (13 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is ￥25,859
￥53,391 total
includes taxes & fees
May 25 - May 26
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
1 bedroom, WiFi

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (3 reviews)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is ￥30,954
￥61,121 total
includes taxes & fees
May 19 - May 20
Luxe Provincial Style Studio w/ Patio & Parking
Interior

Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach
Cove - East Side - Shippan
9.2 out of 10, Wonderful, (24 reviews)
"House was amazing, with a wonderful view. Hosts were responsive and helpful. Will need to come back in summer!"
United States
Scott H.
The price is ￥69,846
￥143,171 total
includes taxes & fees
Jun 14 - Jun 15
Waterview House Walking Distance from Cove Beach
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, (31 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is ￥34,923
￥65,542 total
includes taxes & fees
May 19 - May 20
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Smart TV

THE OASIS @ LONG ISLAND

THE OASIS @ LONG ISLAND
Huntington Station
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay!"
United States
Brandon W.
The price is ￥39,685
￥77,805 total
includes taxes & fees
May 19 - May 20
THE OASIS @ LONG ISLAND
Luxury House | Living area

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
Luxury 3BR Home Game Room Free Parking
Living area

Cheerful Home in Yonkers NY

Cheerful Home in Yonkers NY
Lincoln Park
7.6 out of 10, Good, (4 reviews)
"Nice neighborhood,open concept.Hreat space for my entire family.Kitchen big and spacious. Beds are huge. Definitely will stay here again."
United States
Tanya J.
The price is ￥39,685
￥94,020 total
includes taxes & fees
May 19 - May 20
Cheerful Home in Yonkers NY
1 bedroom, iron/ironing board, free WiFi, bed sheets

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Huntington Station
10.0 out of 10, Exceptional, (7 reviews)
"Enjoyed our recent stay!! Would definitely come back "
United States
Donna S.
The price is ￥29,367
￥59,124 total
includes taxes & fees
May 19 - May 20
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN
Coffee/tea maker, spices

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Huntington
10.0 out of 10, Exceptional, (5 reviews)
"Very clean, modern and comfortable. Host was helpful and a great communicator. We will definitely stay again! "
United States
Tricia H.
The price is ￥36,510
￥68,375 total
includes taxes & fees
Jun 6 - Jun 7
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Smart TV, fireplace, books, stereo

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, (11 reviews)
"This house was so lovely, clean, cozy, and well-appointed - everything we could have asked for for a girls' weekend! And so close to the town of Westport with its excellent restaurants and shops. The best!"
United States
Rebecca H.
The price is ￥33,716
￥83,538 total
includes taxes & fees
May 19 - May 20
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Property grounds

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (18 reviews)
"Great place to stay! "
United States
Megan D.
The price is ￥19,684
￥34,121 total
includes taxes & fees
Jun 1 - Jun 2
Piermont Oasis
Luxury Apartment | Living area

Luxury 3 BR Near NYC with Easy Parking

Luxury 3 BR Near NYC with Easy Parking
2.0 star property
Bryn Mawr
The price is ￥63,850
￥95,085 total
includes taxes & fees
May 19 - May 20
Luxury 3 BR Near NYC with Easy Parking
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)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
The price is ￥22,859
￥49,464 total
includes taxes & fees
May 25 - May 26
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Terrace/patio

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)
"Great location"
United States
Jordan S.
The price is ￥15,001
￥21,405 total
includes taxes & fees
May 19 - May 20
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
1 bedroom, desk, WiFi, bed sheets

Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is ￥22,541
￥42,114 total
includes taxes & fees
May 19 - May 20
Spacious Studio with Pool Table
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 ￥26,859
￥35,658 total
includes taxes & fees
May 20 - May 21
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
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

East Norwich Inn

East Norwich Inn

2/10 Terrible
"The room dirty, the bedsheets smelled of marijuana and the staff was very unfriendly. There are NO elevators so be prepared to walk to the 2nd level. They provided NO accommodations for early check ."
Sue 1-night trip
Posted 1 hour ago
East Norwich Inn

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?

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: This vacation home rental near Old Greenwich is located next to a golf course and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like foosball.

How many vacation rentals will I find in Old Greenwich?

Expedia has 12 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.