Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Find vacation rentals that suit your style
Apartments
Aparthotels
Our top choices for Old Greenwich vacation homes
1. Gem by the water+ firepit and all fenced backyard
Gem by the water+ firepit and all fenced backyardWaterside
10.0 out of 10, Exceptional, (22 reviews)
"Property was exactly what we needed for our stay"
Christopher E.
The price is AED 824
AED 1,633 total
includes taxes & fees
17 Nov - 18 Nov
2. Spacious 3BR Townhome | Garage + Near Downtown
Spacious 3BR Townhome | Garage + Near DowntownWest Side
9.2 out of 10, Wonderful, (9 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
Dave J.
The price is AED 1,010
AED 2,005 total
includes taxes & fees
16 Nov - 17 Nov
3. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.Greenwich
9.8 out of 10, Exceptional, (46 reviews)
"Nice stay"
Christopher J.
The price is AED 630
AED 1,224 total
includes taxes & fees
18 Nov - 19 Nov
4. 5BR Beach Home w/ Fireplaces, Fire Pit & Game Room
5BR Beach Home w/ Fireplaces, Fire Pit & Game RoomCove - East Side - Shippan
10.0 out of 10, Exceptional, (27 reviews)
"Very spacious and nicely decorated"
Linda M.
The price is AED 1,745
AED 3,695 total
includes taxes & fees
1 Dec - 2 Dec
5. Spacious 3BR | Family + Work | Ample Parking
Spacious 3BR | Family + Work | Ample ParkingCove - East Side - Shippan
8.6 out of 10, Excellent, (9 reviews)
"Great location - very spacious and strong AC! host was very communicative and easy to deal with."
Cari B.
The price is AED 856
AED 1,770 total
includes taxes & fees
16 Nov - 17 Nov
6. 5BR Water View Home, Sauna, Game Room, Fire Pit
5BR Water View Home, Sauna, Game Room, Fire PitCove - East Side - Shippan
9.4 out of 10, Exceptional, (32 reviews)
"The property was amazing. The house was clean, beautiful, and well equipped. Plenty of space yet still cozy. Host was very communicative and gracious, had a pleasant experience and will definitely be back!"
Maxx V.
The price is AED 2,068
AED 3,873 total
includes taxes & fees
2 Dec - 3 Dec
7. Coastal 5BR: Billiards, Ping Pong, Fire Pit, Yard
Coastal 5BR: Billiards, Ping Pong, Fire Pit, YardCove - East Side - Shippan
9.6 out of 10, Exceptional, (27 reviews)
"The house was perfect! Plenty of bedding and the kitchen was well appointed. We were there for my fathers memorial and the living room provided a great space for us to connect and talk together. "
Maury A.
The price is AED 1,818
AED 3,561 total
includes taxes & fees
16 Nov - 17 Nov
8. Private Single Fam, walk 2 train/ Theater- Dogs OK
Private Single Fam, walk 2 train/ Theater- Dogs OKGreenwich
The price is AED 853
AED 2,826 total
includes taxes & fees
6 Dec - 7 Dec
9. Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic Views
Greenwich Lakefront Estate -- Private Dock, Designer Kitchen & Panoramic ViewsGreenwich
10.0 out of 10, Exceptional, (2 reviews)
"Great location on the lake which the kids loved. The hosts were very friendly and easy to communicate with. The addition of the outdoor grill was a big plus and we enjoyed many afternoons out on the deck. We would stay again."
Nathan R.
The price is AED 5,135
AED 8,160 total
includes taxes & fees
18 Nov - 19 Nov
10. Captain's Cottage - Cold Spring Harbor Water Views
Captain's Cottage - Cold Spring Harbor Water ViewsCold Spring Harbor
10.0 out of 10, Exceptional, (89 reviews)
"Comfortable beds and close to good food"
Stacey S.
The price is AED 808
AED 1,821 total
includes taxes & fees
17 Nov - 18 Nov
11. Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Nice Cozy Room By Empire City Casino And Cross County Shopping CenterSoutheast Yonkers
8.0 out of 10, Very good, (20 reviews)
"Great location"
Jordan S.
The price is AED 291
AED 395 total
includes taxes & fees
16 Nov - 17 Nov
12. Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
Charming suite with patio, heating, WiFi, free parking in welcoming New RochelleNew Rochelle
10.0 out of 10, Exceptional, (14 reviews)
"Host was very polite and helpful. Excellent condition VRBO."
Drew C.
The price is AED 469
AED 1,062 total
includes taxes & fees
16 Nov - 17 Nov
13. Spacious Retreat with Game Room and Fire Pit
Spacious Retreat with Game Room and Fire PitWest Norwalk
8.6 out of 10, Excellent, (4 reviews)
"We had a wonderful stay."
Linda S.
The price is AED 1,299
AED 2,769 total
includes taxes & fees
18 Nov - 19 Nov
14. Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Ultra-Modern Studio | Near Hospital & NYCIM | WiFiHuntington
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful time for stay."
Logan M.
The price is AED 837
AED 1,494 total
includes taxes & fees
1 Dec - 2 Dec
15. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport BorderHistoric District
10.0 out of 10, Exceptional, (16 reviews)
"The property was very clean, host was excellent. The location is near restaurants, transportation, and grocery stores. Nice place to spend time with friends and family."
Melissa H.
The price is AED 962
AED 2,352 total
includes taxes & fees
17 Nov - 18 Nov
16. Gilded Age Luxury Surrounded by Nature
Gilded Age Luxury Surrounded by NatureCranbury
The price is AED 819
AED 1,487 total
includes taxes & fees
18 Nov - 19 Nov
17. 3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQ
3-bedroom 2-bath house in Norwalk with in-law suite, pool, BBQCranbury
8.8 out of 10, Excellent, (8 reviews)
"Great spot for our family. "
Kevin I.
The price is AED 1,084
AED 2,150 total
includes taxes & fees
19 Nov - 20 Nov
18. Huntington Village 4BR Walkable Sleeps 8
Huntington Village 4BR Walkable Sleeps 8Huntington
10.0 out of 10, Exceptional, (5 reviews)
"The house was in an ideal location! Unfortunately, there was a nor easterner so walking was not an option but on a lovely day, it would be a perfect house to stay in and explore Huntington!
The bedrooms were ideal."
Susan
The price is AED 1,634
AED 2,917 total
includes taxes & fees
16 Nov - 17 Nov
19. Stareway to Heaven in Fairfield
Stareway to Heaven in FairfieldFairfield Beach
The price is AED 2,692
AED 4,042 total
includes taxes & fees
24 Nov - 25 Nov
20. Stareway to Heaven Su
Stareway to Heaven SuFairfield Beach
10.0 out of 10, Exceptional, (25 reviews)
"Great property right on the beach!!!! Very clean and the perfect elevated stay for our weekend Would recommend this property again and again!!!"
Amanda B.
The price is AED 2,266
AED 3,240 total
includes taxes & fees
24 Nov - 25 Nov
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.
Learn more about Old Greenwich
Spend sunny afternoons at Tod's Point Beach where locals gather for swimming and spectacular Long Island Sound views. Explore the charming village center with its independent shops, then head to nearby Greenwich Point Park for scenic coastal trails.
Top reviews in Old Greenwich
Hyatt Regency Greenwich
Hyatt Regency GreenwichOld Greenwich
10/10 Excellent
Really nice rooms and beautiful lounge! Great food! Only issue I had was my tv didn't work (an engineer fixed it but within like 12 hours it wasn't working again) and when I went to the hot tub the jets weren't going so it was just like sitting in a hot bath. Still five stars because it's a great place for the price and the staff is all friendly and room service was delicious.
Briana
