Old Greenwich Holiday Rentals

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Our top choices for Old Greenwich holiday rentals

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
The price is AU$736
includes taxes & fees
1 May - 2 May
Luxury NYC Home Game Room Free Parking

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
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is AU$490
includes taxes & fees
6 May - 7 May
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

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, (75 reviews)
"Location was perfect!"
United States
Linda J P.
The price is AU$680
includes taxes & fees
27 Apr - 28 Apr
Captain's Cottage - Cold Spring Harbor Water Views

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, (32 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is AU$406
includes taxes & fees
28 Apr - 29 Apr
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (84 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is AU$373
includes taxes & fees
11 May - 12 May
DUNE Fairfield Beach

Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Cozy 1-bedroom apartment in Hicksville with WiFi, AC
Hicksville
8.8 out of 10, Excellent, (10 reviews)
"Had a great stay "
United States
Desiree
The price is AU$229
includes taxes & fees
29 Apr - 30 Apr
Cozy 1-bedroom apartment in Hicksville with WiFi, AC

Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
6.0 out of 10, (4 reviews)
"Everything was clean, good communication.. I would like to come back again for sure "
United States
Genesis
The price is AU$420
includes taxes & fees
26 Apr - 27 Apr
Luxury 1BR located in Prime Yonkers Area

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 AU$443
includes taxes & fees
27 Apr - 28 Apr
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

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 AU$569
includes taxes & fees
3 May - 4 May
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

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 AU$523
includes taxes & fees
3 May - 4 May
Luxe Provincial Style Studio w/ Patio & Parking

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 AU$375
includes taxes & fees
26 Apr - 27 Apr
Spacious Studio with Pool Table

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 AU$291
includes taxes & fees
3 May - 4 May
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

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 AU$514
includes taxes & fees
2 May - 3 May
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (16 reviews)
"Cute little place we really enjoyed it and the town"
United States
Ezra S.
The price is AU$294
includes taxes & fees
6 May - 7 May
Piermont Oasis

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 AU$191
includes taxes & fees
27 Apr - 28 Apr
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

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, (10 reviews)
"Clean and host was very helpful and accommodating. Highly recommend! "
United States
Brenna M.
The price is AU$757
includes taxes & fees
26 Apr - 27 Apr
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC

Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC
Bronx
9.4 out of 10, Exceptional, (12 reviews)
"Very accommodating "
United States
Nadia T.
The price is AU$632
includes taxes & fees
30 Apr - 1 May
Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC

Comfortable 1BR Apt / Parking / Perfect for Families & Groups

Comfortable 1BR Apt / Parking / Perfect for Families & Groups
Bryn Mawr
The price is AU$508
includes taxes & fees
27 Apr - 28 Apr
Comfortable 1BR Apt / Parking / Perfect for Families & Groups

Luxury Prime 1BR Oasis in New York

Luxury Prime 1BR Oasis in New York
Bryn Mawr
The price is AU$451
includes taxes & fees
27 Apr - 28 Apr
Luxury Prime 1BR Oasis in New York

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 AU$676
includes taxes & fees
29 Apr - 30 Apr
THE OASIS @ LONG ISLAND
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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Find out more about Old Greenwich

Everything you need to know about Old Greenwich holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Old Greenwich holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Old Greenwich holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Old Greenwich holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Old Greenwich. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Old Greenwich holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Old Greenwich holiday rentals we have selected for you start as low as AU$191 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Old Greenwich rentals

At Expedia, we put the best Old Greenwich holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Old Greenwich rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Old Greenwich holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Old Greenwich. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Modern Luxury Home w GameRoom & Parking: This holiday home rental outside of Old Greenwich is situated near the airport, and has a rooftop terrace and 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 that you can cook with friends or family.

How many holiday rentals will I find in Old Greenwich?

Expedia has 12 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.