Photo by Kate Persad

Search Vacation Homes in Old Greenwich

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
In two weeks
In one month

Compare 284 Vacation Homes in Old Greenwich with updated reviews, rates, and availability.

Waterfront Retreat Center for Health & Wellness

9.6 out of 10, Exceptional, (56)
"Very comfortable stay with lots of room to spread out. Interesting older house with many unique features. We were happy to learn that they recently installed a new furnace and a dishwasher. Lots of cookware and dishes. We spread out over two dining rooms for mealtime which worked well for us. "
Waterfront Retreat Center for Health & Wellness

Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

9.4 out of 10, Exceptional, (8)
"Space was nice. Need top sheets on beds. Noisy location and basement tenant."
The price is SAR 1,126
SAR 1,673 total
includes taxes & fees
19 Jan - 20 Jan
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

Cozy and beautiful house

10.0 out of 10, Exceptional, (20)
"Property owner was great at communicating and the house was perfect!"
Cozy and beautiful house

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (93)
"Dierdre's home was a perfect spot for our family Thanksgiving. Well located, well stocked, and very well cared for!"
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Historic Hideaway with Lake Access!

9.6 out of 10, Exceptional, (13)
"We had a great stay at this fascinating historic house! The house is exactly as described and the hosts were incredibly responsive, even to a last minute request to extend our stay."
Historic Hideaway with Lake Access!

Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

9.8 out of 10, Exceptional, (17)
"This place was super clean and exactly as described. "
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (21)
"Great place all is as described and easy check in check out and host was very responsive."
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (53)
"Cute, well-appointed house, great communication, fun stay!"
The price is SAR 769
SAR 1,596 total
includes taxes & fees
4 Feb - 5 Feb
Captain's Cottage - Cold Spring Harbor Water Views

Luxury 3Bed Private Apartment Near Manhattan

9.2 out of 10, Wonderful, (11)
"Host was very accommodating and easy to communicate with!"
The price is SAR 1,219
SAR 2,000 total
includes taxes & fees
1 Feb - 2 Feb
Luxury 3Bed Private Apartment Near Manhattan

Charming New York Escape Near Central Park!

6.4 out of 10, (7)
"Got dropped off at the H-Mart from the airport and did my shopping and then walked over, as the host mentioned it was within walking distance and they were right! Super convenient. Well laid out, thoughtful instructions, everything was super easy. Ideal location for a couple of adults to stay to attend a convention. Also, there are workspaces in both of the bedrooms, which was a nice touch. "
Charming New York Escape Near Central Park!

Waterview House Walking Distance from Cove Beach

9.0 out of 10, Wonderful, (18)
"This was a late holiday gathering of family members from St. Louis and Rye New York. Great and easy spot to get to. Pretty setting with the water view. I am sure in warmer seasons it be great spot for all the outside amenities. Six adults and one baby. Space nice set up. "
The price is SAR 1,456
SAR 3,196 total
includes taxes & fees
23 Jan - 24 Jan
Waterview House Walking Distance from Cove Beach

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (18)
"We were 9 adult women. There was plenty of space for us to gather as a group as well as sleep. The house is clean and in a great neighborhood. Very easy on and off to the highway to get to our conference in Darien. Highly recommend."
The price is SAR 1,238
SAR 2,922 total
includes taxes & fees
22 Jan - 23 Jan
New Beach Home near Stamford Downtown/Shippan

Lovely Basement with 2 Bedrooms and Kitchen

10.0 out of 10, Exceptional, (14)
"3 of us shared this 2 bedroom basement apartment. Everything was clean and comfortable. There were nice touches of providing some coffee, cereal, snacks and even a half gallon of milk. There was plenty of street parking and the location was very convenient for our needs. I would stay there again. "
Lovely Basement with 2 Bedrooms and Kitchen

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

9.2 out of 10, Wonderful, (5)
"It’s nice to have a place for our family of 5 that actually fits us all. Plenty of space and very clean. Thanks "
The price is SAR 825
SAR 1,816 total
includes taxes & fees
22 Jan - 23 Jan
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed, Near...

TheVictorianBlue|25min to NYC

9.4 out of 10, Exceptional, (3)
"Enough room and bathrooms for all Hostess was gracious and generous God be with you"
The price is SAR 2,830
SAR 4,756 total
includes taxes & fees
19 Jan - 20 Jan
TheVictorianBlue|25min to NYC

Entire House on Scenic Estate with Private Pond in Exclusive Neighborhood

9.8 out of 10, Exceptional, (12)
"The property is beautiful and relaxing! We had everything we needed for a great Thanksgiving. Gustavo was an excellent host who checked in on us for anything we might need. I highly recommend this rental! The pond view is stunning and we had 4 ducks visit. "
Entire House on Scenic Estate with Private Pond in Exclusive Neighborhood

Romance Vacation Sweet Home

9.4 out of 10, Exceptional, (13)
"House is really nice and clean. Centrally located in Levittown near lots of stores and restaurants. Our dog absolutely loved the fenced in yard and it’s perfect for entertaining. The beds were super comfortable and rooms are very roomy. Host was great at communicating with us before, during and after our stay. We will definitely book again if we need to!"
Romance Vacation Sweet Home

Entire house with Hot Tub 25 Mins to Manhattan

9.4 out of 10, Exceptional, (3)
"Nice host and property. We loved it! "
The price is SAR 559
SAR 1,104 total
includes taxes & fees
27 Jan - 28 Jan
Entire house with Hot Tub 25 Mins to Manhattan

Glen Cove Home: Walk to Boardwalk + Dining!

9.0 out of 10, Wonderful, (12)
"I enjoyed everything about this property except the description stated there were 2 steps to enter property. It failed to metro the 15 stairs once you opened the door. My aunt struggled with this so be aware when booking this property if you have accessibility needs. "
Glen Cove Home: Walk to Boardwalk + Dining!

Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train

10.0 out of 10, Exceptional, (11)
"This was our 2nd stay and everything was fantastic once again! Highly recommended!!"
Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train
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.
Don't see what you're looking for?
See all available properties in Old Greenwich
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Old Greenwich

Stamford Suites

3.0 star property
6.8 out of 10, (773)
"It was in walking distance of the event we were going to."
The price is SAR 753
SAR 866 total
includes taxes & fees
29 Jan - 30 Jan
Stamford Suites

Waterfront Retreat Center for Health & Wellness

9.6 out of 10, Exceptional, (56)
"Very comfortable stay with lots of room to spread out. Interesting older house with many unique features. We were happy to learn that they recently installed a new furnace and a dishwasher. Lots of cookware and dishes. We spread out over two dining rooms for mealtime which worked well for us. "
Waterfront Retreat Center for Health & Wellness

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (46)
"Sweet location and they remodeled it nice. However, be warned the bar next door does loud live music and the whole building shakes. Would only reccomend to the young party crowd. Not ideal for families. The manager was nice and did try to offer a refund for a night. Not sure how many people want to hear music vibrating until 2am. Young me would not have cared. Sweet beach access"
The price is SAR 856
SAR 1,191 total
includes taxes & fees
23 Jan - 24 Jan
DUNE Fairfield Beach
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.