Old Greenwich Holiday Rentals

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Our top choices for Old Greenwich holiday rentals

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (78 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
The price is NZ$473
includes taxes & fees
2 Mar - 3 Mar
Luxury 3BR Home Game Room Free Parking

Luxury 1BR located in Prime Yonkers Area

Luxury 1BR located in Prime Yonkers Area
2.0 star property
Bryn Mawr
The price is NZ$431
includes taxes & fees
3 Feb - 4 Feb
Luxury 1BR located in Prime Yonkers Area

Elegant Hideaway with Free Parking

Elegant Hideaway with Free Parking
2.0 star property
White Plains
The price is NZ$456
includes taxes & fees
3 Feb - 4 Feb
Elegant Hideaway with Free Parking

Luxe 1BR Oasis - Prime NY Stay

Luxe 1BR Oasis - Prime NY Stay
2.0 star property
Bryn Mawr
The price is NZ$452
includes taxes & fees
3 Feb - 4 Feb
Luxe 1BR Oasis - Prime NY Stay

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
9.2 out of 10, Wonderful, (10 reviews)
"Everything was just as described. Very comfortable and welcoming. Easy communication and feedback. I would definitely stay again. "
United States
Jacquise H.
The price is NZ$594
includes taxes & fees
3 Feb - 4 Feb
Elegant 2BR Modern Oasis Brand-New Build, Luxe Touches & Lightning-Fast WiFi, AC

Spacious 3BR Luxe Escape near NYC

Spacious 3BR Luxe Escape near NYC
2.0 star property
Southeast Yonkers
"Room was cold. No parking lot for vehicle. Only off-street parking was available "
United States
david
The price is NZ$534
includes taxes & fees
3 Feb - 4 Feb
Spacious 3BR Luxe Escape near NYC

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.6 out of 10, Exceptional, (25 reviews)
"Very kind host very comfortable rooms"
United States
brendan o.
The price is NZ$409
includes taxes & fees
8 Feb - 9 Feb
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
The price is NZ$1,292
includes taxes & fees
3 Feb - 4 Feb
Luxury NYC Home Game Room Free Parking

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 NZ$619
includes taxes & fees
3 Feb - 4 Feb
SECRET HIDEAWAY: LUXURY L.I. STUDIO W/PRIV. ENTRN

Two Wash

Two Wash
2.0 star property
Bryn Mawr
The price is NZ$617
includes taxes & fees
3 Feb - 4 Feb
Two Wash

Uscale 2BR Escape in the Heart of NYC

Uscale 2BR Escape in the Heart of NYC
2.0 star property
Bryn Mawr
The price is NZ$543
includes taxes & fees
3 Feb - 4 Feb
Uscale 2BR Escape in the Heart of NYC

Luxury NYC Home with Free Parking for 12

Luxury NYC Home with Free Parking for 12
4.0 star property
White Plains
The price is NZ$1,130
includes taxes & fees
3 Feb - 4 Feb
Luxury NYC Home with Free Parking for 12

Seabreeze at the beach west beach Stamford ct.

Seabreeze at the beach west beach Stamford ct.
Cove - East Side - Shippan
9.8 out of 10, Exceptional, (10 reviews)
"Fantastic place Very clean, a perfect stay !!!"
United States
bill J.
The price is NZ$721
includes taxes & fees
3 Feb - 4 Feb
Seabreeze at the beach west beach Stamford ct.

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, (74 reviews)
"Perfect space for family. Enjoyed ping pong, walk to the village, hike in the park and view oh the harbor. "
United States
Randall S.
The price is NZ$770
includes taxes & fees
3 Feb - 4 Feb
Captain's Cottage - Cold Spring Harbor Water Views

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (41 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is NZ$686
includes taxes & fees
3 Feb - 4 Feb
Guesthouse at Norwalk Inn

Piermont Oasis

Piermont Oasis
Piermont
9.8 out of 10, Exceptional, (12 reviews)
"Absolutely perfect location--so lovely to walk to restaurants, ice cream, views, etc. Would definitely stay here again."
United States
joelle a.
The price is NZ$344
includes taxes & fees
8 Feb - 9 Feb
Piermont Oasis

Luxury 3BR Family Home Game Room Parking

Luxury 3BR Family Home Game Room Parking
2.0 star property
Bryn Mawr
The price is NZ$617
includes taxes & fees
3 Feb - 4 Feb
Luxury 3BR Family Home Game Room 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 NZ$537
includes taxes & fees
3 Feb - 4 Feb
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

1-bedroom apartment with AC in Syosset

1-bedroom apartment with AC in Syosset
Syosset
The price is NZ$710
includes taxes & fees
8 Feb - 9 Feb
1-bedroom apartment with AC in Syosset
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

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 favorite 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 depends 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 NZ$249 per night. Entering your travel dates in the search wizard you might find 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?

Waterfront Retreat Center for Health & Wellness: This holiday home rental outside of Old Greenwich is located by the ocean, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a terrace, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Old Greenwich?

Expedia has 16 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.