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Compare 373 Vacation Homes in Old Greenwich with updated reviews, rates, and availability.

Historic Connecticut Home w/ Grill & Spacious Yard

10.0 out of 10, Exceptional, (6)
"Very well appointed (Boll & Branch sheets so nice). Great communication from owners. "
Historic Connecticut Home w/ Grill & Spacious Yard

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (56)
"Great home to stay. Beautiful area to explore!"
The price is SAR 743
SAR 1,715 total
includes taxes & fees
9 Apr - 10 Apr
Captain's Cottage - Cold Spring Harbor Water Views

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (27)
"Perfect place and plenty of parking. "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Modern 4BD/3BA w/Parking & deck & 29 min>NYC

9.6 out of 10, Exceptional, (10)
"House was very nice and roomy. Area was nice also. Had an issue upstairs with refrigerator but used downstairs one as a backup."
Modern 4BD/3BA w/Parking & deck & 29 min>NYC

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 1,220
SAR 2,288 total
includes taxes & fees
6 Apr - 7 Apr
Luxury 3Bed Private Apartment Near Manhattan

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

10.0 out of 10, Exceptional, (96)
"House is absolutely perfect! This is our second time staying and we will definitely return. So much charm and warmth. I had the best sleep that I have had in months. All the amenities you could ask for, and more. Terrific convenient location. Host goes above and beyond to make sure we are comfortable. "
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown

Charming 3-bedroom house in Bronx with AC, WiFi

10.0 out of 10, Exceptional, (1)
"Mrs Helen was awesome. Loved her hospitality and she’s only next-door if you need her for anything."
Charming 3-bedroom house in Bronx with AC, WiFi

Over Sized Colonial on Private Road.

9.6 out of 10, Exceptional, (39)
"The home was spacious and provided recreation for kids with hot tub, gym, ping pong, foosball, and game. However, property was advertised as 9 bedrooms and 7 baths. My family looked forward to spreading out but 4 bedrooms with adjoining bathrooms were locked. Text host to see if he would open them but he declined. That was disappointing."
Over Sized Colonial on Private Road.

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

9.4 out of 10, Exceptional, (10)
"We were in town for work so didn't spend much time in the house but it was clean, convenient, easy parking, and a great value. "
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (20)
"Great home with fun ping pong table!"
The price is SAR 1,430
SAR 3,039 total
includes taxes & fees
8 Apr - 9 Apr
New Beach Home near Stamford Downtown/Shippan

Charming 2-bedroom house with AC, WiFi in marvelous Nyack

2.0 star property
Charming 2-bedroom house with AC, WiFi in marvelous Nyack

Glen Cove Home: Walk to Boardwalk + Dining!

9.2 out of 10, Wonderful, (13)
"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!

Westport Gem - walk to shops, dining, town center, pet-friendly

10.0 out of 10, Exceptional, (3)
"After a rough year we were able to get a few days away and at the last minute chose this location. Everything we were looking for was there. The home and grounds were beautiful. The location in Westport was exactly what we wanted: magnificent fall foliage, quiet where the home was but close enough to walk to town and enjoy every aspect of being close by the town for lovely cafes and restaurants. Also, beautiful places were accessible by car in minutes such as Earthplace for trails and nature...
Westport Gem - walk to shops, dining, town center, pet-friendly

Spacious Gorgeous Getaway perfect for family reunion or business

9.8 out of 10, Exceptional, (6)
"The place was plenty big and had so many rooms so all of the atjletes on Team B*REAL had their own space. We loved the huge island in the kitchen and open space to hang out together."
Spacious Gorgeous Getaway perfect for family reunion or business

Cozy and beautiful house

10.0 out of 10, Exceptional, (21)
"A movie was being produced at our home.We needed to relocate for the week.We loved the house. All the rooms were clean & organized . Kitchen was well equipped .We met the neighbors! Lovely people !The only draw back is the stairs. Bathrooms are upstairs & in finished basement , but otherwise lovely"
Cozy and beautiful house

Charming Mamaroneck Home ~ 22 Mi to Manhattan

7.8 out of 10, Good, (11)
"Clean and easy check in--Great Location!"
Charming Mamaroneck Home ~ 22 Mi to Manhattan

Ossining Vacation Rental Near River, Trails & MTA!

8.4 out of 10, Very Good, (7)
"This was our Christmas gathering place for family from 4 states. Beautiful home and location. "
Ossining Vacation Rental Near River, Trails & MTA!

Cozy retreat with fenced in yard—centrally located in the heart of Long Island.

10.0 out of 10, Exceptional, (12)
"We had a wonderful stay at this property! The home was beautiful, well-maintained, and had everything we needed for a comfortable visit. The location was absolutely perfect—convenient to everything we needed to do in Huntington. The host was incredibly responsive and made sure we felt welcome from start to finish. We truly appreciated the attention to detail and would highly recommend this property to anyone looking for a great place to stay. We’d happily return in the future. "
Cozy retreat with fenced in yard—centrally located in the heart of Long Island.

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
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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Other property types in Old Greenwich

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (49)
"Really liked Dune. I had a great room that was on the other side from Sea Grape - bar that could be loud. I heard noting from room 31. Could walk to Post Rd and the beach. Ocean view from room. "
The price is SAR 852
SAR 1,186 total
includes taxes & fees
14 Apr - 15 Apr
DUNE Fairfield Beach

Global Luxury Suites White Plains

3.5 star property
6.6 out of 10, (30)
"Great location, friendly people, great apartment "
Global Luxury Suites White Plains

Stamford Suites

3.0 star property
5.6 out of 10, (24)
"Room was very spacious "
The price is SAR 677
SAR 779 total
includes taxes & fees
13 Apr - 14 Apr
Stamford Suites
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.