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Old Greenwich Holiday Rentals

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Holiday Rentals in Old Greenwich

Stamford Suites

4.0 star property
5.8 out of 10, (64)
"Location very good."
The price is AU$235
includes taxes & fees
19 Oct - 20 Oct
Stamford Suites

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (72)
"Loved this venue! "
DUNE Fairfield Beach

3BR Prime Luxury near NYC w Arcade Room

2.0 star property
8.0 out of 10, Very good, (1)
"We thought we rented the entire property, but was half of it. expect a lot of stairs. No bath tubs but two showers. some door knobs and locks need maintenance, but overall nice clean rooms."
The price is AU$1,188
includes taxes & fees
14 Oct - 15 Oct
3BR Prime Luxury near NYC w Arcade Room

Global Luxury Suites White Plains

3.5 star property
6.8 out of 10, (32)
"Being in an apartment building for an actual stay instead of a house was a first for myself and the family but overall a good stay."
Global Luxury Suites White Plains

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

9.6 out of 10, Exceptional, (17)
"Perfect place to rest. Excellent service! "
The price is AU$317
includes taxes & fees
17 Oct - 18 Oct
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"it was amazing will stay again food was good comfort was great "
The price is AU$461
includes taxes & fees
30 Oct - 31 Oct
Guesthouse at Norwalk Inn

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (18)
"This place truly felt like a home away from home. Everything was spotless, comfortable, and well cared for. The location made it easy to access everything we needed, whether dining, shopping, or exploring the area. I would definitely return!"
Luxury Apartments by Hyatus at The Asher

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

9.8 out of 10, Exceptional, (10)
"Everything was very clean and cozy.We have enjoyed our stay there. "
Luxury New-Build 2BR w King Bed, Designer Finishes + Ultra-Fast WiFi & AC

Modern Luxury Home w GameRoom & Parking

3.0 star property
7.2 out of 10, Good, (5)
"Put down a deposit with the understanding that the deposit would be back in my account within 24 hours. Messaged them several times and I have not gotten any response nor have I gotten my money back and it has been days now with no response. Apartment was filthy, beds were used and not cleaned, bunch of appliances didn’t work, found a towel with stains potentially from bodily fluids.DO NOT BOOK WITH THEM THEY ARE SCAMMERS. Charged a cleaning fee on top of this for an apartment that wasn’t even...
Modern Luxury Home w GameRoom & Parking

Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

9.0 out of 10, Wonderful, (2)
"The owner was very responsive and kind. The apartment was very clean and well updated. We are older adults and the access to the basement apartment was a bit of a challenge but the owner did graciously help with our luggage. The family does clearly disclose that they live above the unit and sounds of children may be heard. Between the sounds of the family above and the fact it’s a basement, not a “Loft”, with all the plumbing just above your head - it was not for us. "
The price is AU$503
includes taxes & fees
15 Oct - 16 Oct
Loft Apartment with full kitchen cozy nook + 2 sofa beds & all modern electronic

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

8.8 out of 10, Excellent, (40)
"Very clean, comfortable, and quiet property. Although advertised one car parking, actually can park 2, which is good since limited street parking in a crowded neighborhood. Highly recommended if you're staying in the NYC area."
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

9.6 out of 10, Exceptional, (10)
"Easy check in and check out! Has all the bare minimums and a nicely upgraded bathroom. Didn’t feel super clean (the bathroom) when we got there but kitchen was clean and they kindly stocked a few groceries. Could not get the water hot for a shower which was bummer. Nice enough depending on what you are looking for! We had some sensory needs and so this ended up not being the best fit but the location was great. Thanks for having us. "
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

Luxury Living in the Heart of NY

4.0 star property
2.0 out of 10, (1)
"The photos of the unit were beautiful however the wear and tear on the actual property did not compare. The bathroom sink constantly leaked and because the floors were not even they stayed wet. The nightstands were broken the refrigerator would not open all the way. I also was not notified until the day of check in that the unit was on the 3rd floor and there was 2 flights of stairs just to get to the entrance to the unit."
Luxury Living in the Heart of NY

Elegant Hideaway • Free Parking

Elegant Hideaway • Free Parking

price will make you book twice , luxury living

10.0 out of 10, Exceptional, (1)
"We had a great stay! Room was very open and clean and our host was friendly and welcoming! "
The price is AU$258
includes taxes & fees
14 Oct - 15 Oct
price will make you book twice , luxury living

Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

9.0 out of 10, Wonderful, (6)
"Large comfortable home in great location with multiple views of the Hudson. Our family had a pleasant stay and would definitely return to Castle in the Sky."
Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

Nice Cozy Room By Empire City Casino And Cross County Shopping Center

8.0 out of 10, Very good, (17)
"Great place great location"
The price is AU$211
includes taxes & fees
21 Oct - 22 Oct
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Comfortable 1 family home in Tuckahoe that's near train

The price is AU$1,104
includes taxes & fees
14 Oct - 15 Oct
Comfortable 1 family home in Tuckahoe that's near train

Luxury 5BR 2BA Spacious Home NYC Free Parking + Office

2.0 out of 10, (2)
"We did not stay due in the property at all because of a gas leak that they notified 4:15pm the day of check in. They would not give us the code to the address until 4:20 after saying everything was fixed. We went into property and in 5 minutes, headache and eye tearing. The host lied to us and informed us that there was no gas leak, only to produce a certificate that day that they sent someone out to check about the gas leak. Host was disrespectful, he kept saying the leak was at another...
Luxury 5BR 2BA Spacious Home NYC Free Parking + Office

Beautiful Waterfront 3 Bedroom 1.5 Bath Beach Home Sunset Oasis Village 1hr NYC

9.2 out of 10, Wonderful, (11)
"Perfect location to enjoy Northport! Everything is within walking distance. Host was very helpful and accommodating. Great stay and will definitely return! "
The price is AU$965
includes taxes & fees
15 Oct - 16 Oct
Beautiful Waterfront 3 Bedroom 1.5 Bath Beach Home Sunset Oasis Village 1hr NYC
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 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$211 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?

3BR Prime Luxury near NYC w Arcade Room: This holiday home rental outside of Old Greenwich is near the airport and offers free WiFi to help you feel perfectly comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals will I find in Old Greenwich?

Expedia has 14 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.