Holiday Homes in 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

Featured Holiday Homes in Greenwich and around

Lower Lvl Private 2BR/1BA Family/Pet Friendly

10.0 out of 10, Exceptional, (115)
"Enjoyed the theater room and the comfortable bed"
Lower Lvl Private 2BR/1BA Family/Pet Friendly

Welcome to Villa Seabird, Luxury Escape on Long Island Sound

10.0 out of 10, Exceptional, (9)
"This was amazing Thanksgiving with my family. The house is amazing Jon was amazing host and his recommendation for food made you feel like million dollars. Can not thank you enough to share your beautiful home with us and see you in the summer."
Welcome to Villa Seabird, Luxury Escape on Long Island Sound

Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury

9.4 out of 10, Exceptional, (8)
"Great place for a group of friends to use as homebase for some shows at the Capitol Theater. "
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury

Waterview House Walking Distance from Cove Beach

9.0 out of 10, Wonderful, (16)
"The house is beautiful, amazing views! Communication was punctual."
The price is €1,009
includes taxes & fees
16 Jan - 17 Jan 2025
Waterview House Walking Distance from Cove Beach

New Beach Home near Stamford Downtown/Shippan

10.0 out of 10, Exceptional, (16)
"Exactly as advertised, great location, easy check-in, hosts responded immediately to questions. Recommended."
The price is €1,046
includes taxes & fees
30 Dec - 31 Dec
New Beach Home near Stamford Downtown/Shippan

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 €481
includes taxes & fees
6 Jan - 7 Jan 2025
Modern 3 Bdrm Home w/ Parking, Park Views, Backyard, King Bed | Near...

Charming duplex with private yard. Close to the beach, dining & shopping!

9.8 out of 10, Exceptional, (36)
"Duplex unit was clean, as described and perfect for our stay visiting family in Rye. Lots of extra towels and nice welcoming snacks in the kitchen. Super convenient location. Will likely stay there again. "
Charming duplex with private yard. Close to the beach, dining & shopping!

ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home

10.0 out of 10, Exceptional, (24)
"Pre-stay communication was excellent, with our host contacting me with suggestions for outings (I asked). Our host met us, gave us a tour of the property - not just the living space but the grounds, too. The house is cozy, well thought out and has small touches like a deck of cards (in case you have a couple of minutes of downtime), a beautiful tea set with a variety of delicious teas to use. The house is thoughtfully decorated, the couch and bed are comfortable and there is plenty of space for...
ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home

Beautiful downstairs apartment. Walk to town, train, & beach ferry!

10.0 out of 10, Exceptional, (18)
"We had a wonderful day. The location is fantastic with easy access to restaurants and the rest of Greenwich. The place itself is well appointed and in good shape. We would absolutely stay here again. Loved it. (neighbors upstairs stomp around a bit!)"
Beautiful downstairs apartment. Walk to town, train, & beach ferry!

Spacious 3b/3b Mediterranean in White Plains

9.6 out of 10, Exceptional, (10)
"Very beautiful and spacious home. Super clean and amenities galore. Quiet and peaceful neighborhood. Very well kept and loved the white picket fence. Felt very safe."
Spacious 3b/3b Mediterranean in White Plains

Beautiful 5 bedroom Darien house with pool

Beautiful 5 bedroom Darien house with pool

Quaint duplex with private yard. Walk to beach, dining, & shopping!

10.0 out of 10, Exceptional, (38)
"This was a perfect location for us to stay having travelled from the UK to spend time with family in nearby Greenwich. We appreciated the comfortable and clean surroundings. The beds were comfortable and plenty of towels. We very much enjoyed having a kettle being tea loving brits! Henri was very responsive to our booking and communications were excellent. We would definitely stay again! "
Quaint duplex with private yard. Walk to beach, dining, & shopping!

The Fred Deluxe 7 BR by I95, Train, HarborVw Beach

9.0 out of 10, Wonderful, (6)
"Overall it was a good stay for my work team."
The price is €1,036
includes taxes & fees
2 Jan - 3 Jan 2025
The Fred Deluxe 7 BR by I95, Train, HarborVw Beach

Upscale Super LUX Private 2br Near NYC

2.0 out of 10, (1)
"The sheets were way over bleached and burned my skin. The bed is way too soft and the sofa is uneven and sinks. The area is quite scary especially at night, and it is surrounded by vacant lots and construction zones. Most of the other stores in this building are closed, and homeless people walking around. The cleaning products use have a distinctively bad smell that even the air conditioning couldn’t eliminate, and the air conditioners are so loud you can’t hear the tv if they are running."
The price is €284
includes taxes & fees
6 Jan - 7 Jan 2025
Upscale Super LUX Private 2br Near NYC

2 mini-bedrooms apartment with antique bathtub.

10.0 out of 10, Exceptional, (19)
"Conveniently located to small downtown area & train into NYC. "
2 mini-bedrooms apartment with antique bathtub.

Remodeled 3 Bedroom home in the heart of Stamford

5.0 out of 10, (2)
"So the house is advertised as 4 bedroom but one of the rooms is an attic room with a trundle bed we didn’t really find suitable for any of our guests during the stay. Minimal furniture and some ant problems in the kitchen The in and out of the house was super nice plus the bathroom situation was great. Did the job sorta for what we needed (someone had to bring an air mattress though) but wouldn’t stay again"
Remodeled 3 Bedroom home in the heart of Stamford

3-LEVEL RETRO HOUSE/CLOSE TO BEACH, NYC, STAMFORD, WESTPORT, GREENWICH

10.0 out of 10, Exceptional, (14)
"Met our needs to have multiple beds in a good location. Good tv. Well equipped kitchen "
3-LEVEL RETRO HOUSE/CLOSE TO BEACH, NYC, STAMFORD, WESTPORT, GREENWICH

Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail

10.0 out of 10, Exceptional, (34)
"Our stay at Gersende's property was delightful. We had seven friends together for a wedding and this house and property served as a much appreciated comfortable and peaceful retreat. The pool was lovely, the kitchen was well-stocked and functional and the homes quirks and charm grew on us a little more each day. We walked to GrayBarns Mercantile every morning for coffee and it was a quick drive from the grocery as well as the PJ Glass House. Gersende was kind, easy to reach and incredibly...
Private French Country Estate-New Canaan CT-Pool-Film Set-Dec avail

St Julian's Place - Large updated Apt @ 40 Min NYC

10.0 out of 10, Exceptional, (33)
"This is the 3rd time we've stayed here. The apartment looks great and is convenient for us to visit family. We always enjoy staying here."
St Julian's Place - Large updated Apt @ 40 Min NYC

Stylish Beach Home near Stamford Downtown/Beach

10.0 out of 10, Exceptional, (19)
"Lovely place, great location, had absolutely everything we needed! Would absolutely stay here again. "
The price is €1,259
includes taxes & fees
27 Dec - 28 Dec
Stylish Beach Home near Stamford Downtown/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.
Don't see what you're looking for?
See all available properties in Greenwich
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Greenwich

Radio City Apartments

3.5 star property
8.8 out of 10, Excellent, (3951)
"I will definitely be staying there again."
The price is €100
includes taxes & fees
22 Jan - 23 Jan 2025
Radio City Apartments

31 Street Broadway Hotel

2.0 star property
5.4 out of 10, (977)
"Clean, comfortable, affordable, no problems. I would stay here again."
The price is €196
includes taxes & fees
14 Jan - 15 Jan 2025
31 Street Broadway Hotel

Starlight Hotel

2.5 star property
8.2 out of 10, Very good, (388)
"Great people nice overall "
The price is €194
includes taxes & fees
14 Jan - 15 Jan 2025
Starlight Hotel
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.