Photo by Kate Persad

Search Vacation Homes in Old Greenwich

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Vacation Homes in Old Greenwich

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 SAR 250
SAR 707 total
includes taxes & fees
12 Oct - 13 Oct
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

10.0 out of 10, Exceptional, (5)
"Great space! Very clean & well appointed! If you forgot to pack it, it is probably there!"
The price is SAR 769
SAR 1,496 total
includes taxes & fees
13 Oct - 14 Oct
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (68)
"Great home to stay. Beautiful area to explore!"
The price is SAR 975
SAR 2,057 total
includes taxes & fees
13 Oct - 14 Oct
Captain's Cottage - Cold Spring Harbor Water Views

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 SAR 354
SAR 506 total
includes taxes & fees
21 Oct - 22 Oct
Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

10.0 out of 10, Exceptional, (5)
"Lovely little home in Stamford."
The price is SAR 656
SAR 1,332 total
includes taxes & fees
23 Oct - 24 Oct
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

2.0 star property
10.0 out of 10, Exceptional, (7)
"The house was exactly as presented on the website. 4 good size bedrooms, all with very comfortable king size beds, that is typically hard to find! Fantastic sunlit kitchen nook. Good location, easy access to I-95 and Parkway. "
The price is SAR 1,031
SAR 2,279 total
includes taxes & fees
27 Oct - 28 Oct
Norwalk/Westport Border, Near Beach, w/Fire Pit, 60 Min to NYC

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

9.0 out of 10, Wonderful, (2)
"the home was nice clean if in the area I would stay here again"
The price is SAR 863
SAR 1,877 total
includes taxes & fees
13 Oct - 14 Oct
Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Stylish Beach Home near Stamford Downtown/Beach

10.0 out of 10, Exceptional, (23)
"Everything was great"
The price is SAR 1,414
SAR 3,051 total
includes taxes & fees
15 Oct - 16 Oct
Stylish Beach Home near Stamford Downtown/Beach

45 Minutes from NYC, Entire House near Stamford Downtown,

10.0 out of 10, Exceptional, (18)
"Very nice property. Owner was very nice and quickly answered any questions we had. Well stocked pantry and fridge!! We enjoyed our stay and property was very convenient and comfortable. "
The price is SAR 1,069
SAR 2,000 total
includes taxes & fees
16 Oct - 17 Oct
45 Minutes from NYC, Entire House near Stamford Downtown,

Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

9.2 out of 10, Wonderful, (5)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
The price is SAR 1,140
SAR 2,234 total
includes taxes & fees
13 Oct - 14 Oct
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

Cheerful Home in Yonkers NY

7.6 out of 10, Good, (4)
"Nice neighborhood,open concept.Hreat space for my entire family.Kitchen big and spacious. Beds are huge. Definitely will stay here again."
Cheerful Home in Yonkers NY

Charming 3-bedroom modern family retreat!

9.2 out of 10, Wonderful, (5)
The price is SAR 1,384
SAR 2,053 total
includes taxes & fees
12 Oct - 13 Oct
Charming 3-bedroom modern family retreat!

TheVictorianBlue|25min to NYC

9.6 out of 10, Exceptional, (5)
"The accommodations were fantastic, with spacious rooms, modern amenities, and breathtaking views. Additionally, the host was incredibly accommodating, ensuring that every aspect of my stay was comfortable and enjoyable. I highly recommend this property to anyone looking for a perfect getaway with a gracious host!"
The price is SAR 2,564
SAR 4,549 total
includes taxes & fees
13 Oct - 14 Oct
TheVictorianBlue|25min to NYC

Comfortable 1 family home in Tuckahoe that's near train

The price is SAR 1,463
SAR 2,640 total
includes taxes & fees
12 Oct - 13 Oct
Comfortable 1 family home in Tuckahoe that's near train

The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace

8.6 out of 10, Excellent, (7)
"Overall it was a good stay for my work team."
The price is SAR 1,612
SAR 3,313 total
includes taxes & fees
16 Oct - 17 Oct
The Fred Deluxe 7 BR by I95, Train, HarborVw, Stamford Beaches & Workspace

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (21)
"Great stay!"
The price is SAR 1,947
SAR 3,561 total
includes taxes & fees
14 Oct - 15 Oct
New Beach Home near Stamford Downtown/Shippan

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 SAR 2,247
SAR 2,885 total
includes taxes & fees
12 Oct - 13 Oct
3BR Prime Luxury near NYC w Arcade Room

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 SAR 1,509
SAR 2,337 total
includes taxes & fees
15 Oct - 16 Oct
Beautiful Waterfront 3 Bedroom 1.5 Bath Beach Home Sunset Oasis Village 1hr NYC

Spacious 4-bedroom house in serene East Northport. 25 minutes from RYDER cup!

2.0 star property
Spacious 4-bedroom house in serene East Northport. 25 minutes from RYDER cup!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

8.8 out of 10, Excellent, (5)
"We booked the property because our family is growing too large for all of the children and grandchildren to spend the holidays together. The “holiday house” as our 4 year old coined it was the perfect place to spend Christmas and Hanukkah. Large yet cozy and very well appointed. All of our communication with proprietors was prompt and helpful, and they had the driveway salted and plowed within hours of the (very picturesque) snowfall the day before Christmas. I would happily book here again. "
The price is SAR 3,154
SAR 5,117 total
includes taxes & fees
16 Oct - 17 Oct
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Old Greenwich Hotel Reviews