Holiday Homes in Old Greenwich

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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Old Greenwich holiday homes

Property grounds

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, (36 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is €278
includes taxes & fees
10 Jun - 11 Jun
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Property grounds

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

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.2 out of 10, Wonderful, (15 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is €310
includes taxes & fees
9 Jun - 10 Jun
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Outdoor dining

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
Huntington
9.8 out of 10, Exceptional, (7 reviews)
"Host was very accommodating - lovely property!"
United States
Mary C.
The price is €197
includes taxes & fees
8 Jul - 9 Jul
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
Terrace/patio

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

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
The price is €121
includes taxes & fees
8 Jun - 9 Jun
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Marina

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (78 reviews)
"A true port in the storm"
United States
Trey S.
The price is €512
includes taxes & fees
15 Jun - 16 Jun
Captain's Cottage - Cold Spring Harbor Water Views
Hair dryer, towels, soap, toilet paper

Jericho Luxe Retreat

Jericho Luxe Retreat
Jericho
10.0 out of 10, Exceptional, (1 review)
"My family and I had a great stay! Perfect location!"
United States
Maurice Joen R.
Jericho Luxe Retreat
TV, books, offices

Bright&Comfy 2bed/1ba in quiet White Plains duplex

Bright&Comfy 2bed/1ba in quiet White Plains duplex
White Plains
8.8 out of 10, Excellent, (6 reviews)
"Location was great! Clean house! Comfy beds! Great space! "
United States
Montana M.
Bright&Comfy 2bed/1ba in quiet White Plains duplex
Coffee/tea maker, spices

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi

Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Huntington
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful time for stay."
United States
Logan M.
The price is €345
includes taxes & fees
15 Jun - 16 Jun
Ultra-Modern Studio | Near Hospital & NYCIM | WiFi
Living area

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
The price is €320
includes taxes & fees
7 Jul - 8 Jul
Stamford Hideaway w/ Fire Pit
Interior

Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach
Cove - East Side - Shippan
9.2 out of 10, Wonderful, (25 reviews)
"House was amazing, with a wonderful view. Hosts were responsive and helpful. Will need to come back in summer!"
United States
Scott H.
The price is €759
includes taxes & fees
14 Jun - 15 Jun
Waterview House Walking Distance from Cove Beach
Fridge, microwave, oven, stovetop

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

Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train
Fairfield Beach
10.0 out of 10, Exceptional, (24 reviews)
"Host was great. Had a great stay. "
United States
jeff d.
Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train
Fridge, microwave, stovetop, dishwasher

NYC-Area Escape Near River, Trails & MTA!

NYC-Area Escape Near River, Trails & MTA!
Ossining
7.8 out of 10, Good, (16 reviews)
"Host was very communicative. "
United States
Joe W.
The price is €771
includes taxes & fees
14 Jun - 15 Jun
NYC-Area Escape Near River, Trails & MTA!
TV, fireplace, table football, offices

New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (24 reviews)
"Excellent home, met all expectations, and attentive staff"
United States
Steve G.
The price is €877
includes taxes & fees
10 Jun - 11 Jun
New Beach Home near Stamford Downtown/Shippan
Fridge, microwave, oven, stovetop

Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (25 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. "
United States
Maury A.
Stylish Beach Home near Stamford Downtown/Beach
Fridge, microwave, oven, stovetop

Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
The price is €533
includes taxes & fees
8 Jun - 9 Jun
Spacious Retreat with Game Room and Fire Pit
Interior

6 BR, 4 BA Mansion Close to the City

6 BR, 4 BA Mansion Close to the City
Getty Square
8.0 out of 10, Very good, (3 reviews)
"Great location and house"
United States
Megan T.
The price is €753
includes taxes & fees
9 Jun - 10 Jun
6 BR, 4 BA Mansion Close to the City
Interior

Walkable Townhouse with Garage & Yard, 45 min to NYC!

Walkable Townhouse with Garage & Yard, 45 min to NYC!
West Side
9.4 out of 10, Exceptional, (6 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
The price is €706
includes taxes & fees
14 Jun - 15 Jun
Walkable Townhouse with Garage & Yard, 45 min to NYC!
Exterior

The Victorian Blue 25min to NYC

The Victorian Blue 25min to NYC
North Side
9.8 out of 10, Exceptional, (8 reviews)
"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!"
United States
Honna C.
The price is €1,163
includes taxes & fees
8 Jun - 9 Jun
The Victorian Blue 25min to NYC
Dining

Spacious 3BR Home / Free Parking / Perfect for Families & Groups

Spacious 3BR Home / Free Parking / Perfect for Families & Groups
White Plains
The price is €1,880
includes taxes & fees
8 Jul - 9 Jul
Spacious 3BR Home / Free Parking / Perfect for Families & Groups
Exterior

World Cup Rental Waterfront Beach House Sunsets Private 90 mins MetLife

World Cup Rental Waterfront Beach House Sunsets Private 90 mins MetLife
Northport
9.4 out of 10, Exceptional, (16 reviews)
"Great host and property!"
United States
Anonymous traveller
The price is €1,556
includes taxes & fees
22 Jun - 23 Jun
World Cup Rental Waterfront Beach House Sunsets Private 90 mins MetLife
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

Tarrytown House Estate

Tarrytown House Estate

8/10 Good
"Good hotel, room and common area are outdated, popcorns ceilings and white lights in rooms. the hairdryer is straight out for the 80’. Buffett breakfast was ok. The property is beautiful and the outdoor pool is amazing. We enjoy our stay."
Elisa 1-night trip
Posted less than an hour ago
Tarrytown House Estate

Find out more about Old Greenwich

Old Greenwich Holiday Homes information

Number of reviews
314
Accommodation
379 Holiday Homes
Lowest Price
€121
Highest Price
€1,880