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Old Greenwich Holiday Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sept - 20 Sept
In four months
16 Oct - 18 Oct

Our top choices for Old Greenwich holiday rentals

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, (96 reviews)
"Stayed for a night but had a good experience"
United States
Deanna
The price is HK$1,597
HK$2,315 total
includes taxes & fees
14 Jul - 15 Jul
DUNE Fairfield Beach
2 bedrooms, iron/ironing board, WiFi, bed sheets

Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC
Bronx
9.8 out of 10, Exceptional, (26 reviews)
The price is HK$2,117
HK$4,239 total
includes taxes & fees
1 Jul - 2 Jul
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC
Dining

Modern Comfort in the Heart of NYC

Modern Comfort in the Heart of NYC
4.0 star property
Southeast Yonkers
2.0 out of 10, (3 reviews)
"We never got to stay because THERE WAS ANOTHER FAMILY THERE. THAT WOMEN SAID SHE WAS RENTING THE HOUSE FOR ANOTHER MONTH. "
United States
Angel
The price is HK$3,175
HK$4,720 total
includes taxes & fees
29 Jun - 30 Jun
Modern Comfort in the Heart of NYC
Living area

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
8.0 out of 10, Very good, (2 reviews)
"Room was cold. No parking lot for vehicle. Only off-street parking was available "
United States
david
The price is HK$3,528
HK$5,115 total
includes taxes & fees
28 Jun - 29 Jun
Spacious 3BR Luxe Escape near NYC
Interior

3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home
3.0 star property
White Plains
The price is HK$1,435
HK$5,577 total
includes taxes & fees
14 Jul - 15 Jul
3 Mi to Downtown: Spacious White Plains Home
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, (41 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is HK$1,517
HK$2,756 total
includes taxes & fees
29 Jun - 30 Jun
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
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, (15 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is HK$1,686
HK$3,163 total
includes taxes & fees
28 Jun - 29 Jun
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
In-room safe, iron/ironing board, travel cot, free WiFi

2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly

2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
Bryn Mawr
The price is HK$3,175
HK$5,853 total
includes taxes & fees
29 Jun - 30 Jun
2BR House w/ Free Parking / Fully Equipped Kitchen / Spacious / Family Friendly
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, (80 reviews)
"A true port in the storm"
United States
Trey S.
The price is HK$2,979
HK$5,527 total
includes taxes & fees
7 Jul - 8 Jul
Captain's Cottage - Cold Spring Harbor Water Views
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 HK$1,725
HK$3,282 total
includes taxes & fees
13 Jul - 14 Jul
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Smart TV

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
10.0 out of 10, Exceptional, (6 reviews)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
United States
danyelle s.
The price is HK$2,462
HK$5,650 total
includes taxes & fees
1 Jul - 2 Jul
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
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 HK$1,105
HK$1,860 total
includes taxes & fees
7 Jul - 8 Jul
Piermont Oasis
Living area

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
The price is HK$988
HK$2,635 total
includes taxes & fees
29 Jun - 30 Jun
Stamford Hideaway w/ Fire Pit
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 HK$1,129
HK$3,274 total
includes taxes & fees
4 Jul - 5 Jul
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 HK$1,129
HK$2,459 total
includes taxes & fees
29 Jun - 30 Jun
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Smart TV

Perfect Family Getaway / 5BR Home / 6 Queen Beds / Free Parking

Perfect Family Getaway / 5BR Home / 6 Queen Beds / Free Parking
Bryn Mawr
The price is HK$6,350
HK$10,127 total
includes taxes & fees
28 Jun - 29 Jun
Perfect Family Getaway / 5BR Home / 6 Queen Beds / Free Parking
1 bedroom, iron/ironing board, free WiFi, bed sheets

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 HK$741
HK$1,057 total
includes taxes & fees
28 Jun - 29 Jun
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Interior

What's headline

What's headline
South Side
The price is HK$1,411
HK$4,829 total
includes taxes & fees
27 Jun - 28 Jun
What's headline
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 HK$1,764
HK$2,350 total
includes taxes & fees
29 Jun - 30 Jun
Private Gazebo on Byram River, Naturally Preserved your own stone deck Greenwich
Terrace/patio

Spacious 3BR Home • Free Parking • Convenient NYC Access • Perfect for Families

Spacious 3BR Home • Free Parking • Convenient NYC Access • Perfect for Families
Southeast Yonkers
The price is HK$2,470
HK$4,911 total
includes taxes & fees
30 Jun - 1 Jul
Spacious 3BR Home • Free Parking • Convenient NYC Access • Perfect for Families
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

Westchester Marriott

Westchester Marriott

10/10 Excellent
"."
Michael 1-night trip
Posted 12 hours ago
Westchester Marriott

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 holiday rentals in Old Greenwich?

Yes, there are holiday rentals close to the most popular sights in Old Greenwich, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the top-notch restaurants and shops in Old Greenwich. Make sure you have time to check out the beaches and cafés during your trip.

What are some of the best holiday rentals that Old Greenwich has to offer?

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

How many holiday rentals will I find in Old Greenwich?

Expedia has 13 holiday 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 holiday rentals like in Old Greenwich?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Old Greenwich. Holiday rentals provide amenities such as WiFi and washers and dryers so you'll feel just like you're staying in your own home. If you're concerned about a clean environment, holiday rentals can offer a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you to travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family gatherings.