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Compare 38 Cottages in Old Greenwich with updated reviews, rates, and availability.

California cozy cottage/studio in the middle of the Greenwich
Outdoor dining

California cozy cottage/studio in the middle of the Greenwich

10.0 out of 10, Exceptional, (2)
"This VRBO was a pleasure! Host Olga was very accommodating. This was my first VRBO experience and I will definitely do this again. So much nicer than a hotel stay. It was a wonderful 5 days! I would highly recommend Olga and her California Cottage. "
California cozy cottage/studio in the middle of the Greenwich
Westport "Gold Coast" across from Southport beach
Property grounds

Westport "Gold Coast" across from Southport beach

10.0 out of 10, Exceptional, (83)
"The property was perfectly located for my needs, nicely appointed, comfortable furnishings, spacious, nice light, and felt like home."
Westport "Gold Coast" across from Southport beach
Beach house cottage steps to private beach in the heart of Bayville
Beach

Beach house cottage steps to private beach in the heart of Bayville

10.0 out of 10, Exceptional, (9)
"Great location. Very clean modern cottage by the sea. Would love to stay again. "
Beach house cottage steps to private beach in the heart of Bayville
Wow Waterfront Sunset Oasis Beach Cottage Village Winery Brewery East End NYC Hr
Miscellaneous

Wow Waterfront Sunset Oasis Beach Cottage Village Winery Brewery East End NYC Hr

9.0 out of 10, Wonderful, (7)
"Very cute cottage on the water with a deck and beautiful views. A short walk into town to shops and restaurants. "
Wow Waterfront Sunset Oasis Beach Cottage Village Winery Brewery East End NYC Hr
Adorable 1-Bedroom Cottage in Weston, CT
Living-Room view from Mezzanine

Adorable 1-Bedroom Cottage in Weston, CT

10.0 out of 10, Exceptional, (36)
"beautiful cottage with all the amenities you need.. charming historic property.. would highly recommend "
The price is SAR 732
SAR 1,128 total
includes taxes & fees
4 Jan - 5 Jan
Adorable 1-Bedroom Cottage in Weston, CT
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Exterior

Historic Pound Ridge Cottage, 2 Beds, Fully Furnished

9.4 out of 10, Exceptional, (3)
"I spent 2 serene weeks here and hope to return some day! With modern creature comforts in the kitchen, the rest of this home is very rustic. If you are looking for peace and quiet, and are into drawing, cooking or reading books to the sounds of trees rustling and water flowing across the street, you will be in heaven here. For summer months, note that there is only a small portable AC unit in the sunroom. There are several fans and it was manageable in early summer, but I imagine it is quite...
Historic Pound Ridge Cottage, 2 Beds, Fully Furnished
Trendy 1 bedroom +loft apartment w/ parking
Interior

Trendy 1 bedroom +loft apartment w/ parking

10.0 out of 10, Exceptional, (5)
"This was our home base while we explored NYC. The place was lovely and well-appointed. It’s almost a shame that we hardly spent any time there. Just in and out to sleep, shower and eat breakfast, then back to the commuter train into NYC. Found free unlimited street parking a few blocks from the train station. Appreciated access to laundry on our last morning to start the next leg of our trip with fresh clothes. "
Trendy 1 bedroom +loft apartment w/ parking
Second floor cottage apartment located in a private community.
Living Room with view towards Bedroom 1

Second floor cottage apartment located in a private community.

9.6 out of 10, Exceptional, (14)
"What a lovely apartment hidden away on a private street. It is very clean and well-kept, and extra attention is given to making sure guests have what they need. Communication with hosts was easy and straightforward. We were very pleased with our stay. "
Second floor cottage apartment located in a private community.
Beachfront cottage located in the heart of Fairfield Beach!!
Outdoor dining

Beachfront cottage located in the heart of Fairfield Beach!!

9.6 out of 10, Exceptional, (15)
"This is my third year staying at this property. I have friends that live around the area so it is a nice quiet private space to reconnect. Paul the host is always quick to respond to any concerns I may have while staying. My dog Angel is in heaven literally 5 steps to the water . The beach and people are so kind and friendly. Love it!"
Beachfront cottage located in the heart of Fairfield Beach!!
Charming New York Escape Near Central Park!
Private kitchen

Charming New York Escape Near Central Park!

3.0 star property
Charming New York Escape Near Central Park!
Sun and Fun on the beach!!
You are here!

Sun and Fun on the beach!!

9.6 out of 10, Exceptional, (15)
"Very good place on the beach….and beach walking Paul communication was very timely"
Sun and Fun on the beach!!
South Salem Vacation Rental w/ Furnished Deck!
South Salem Vacation Rental | 1BR | 1BA | Stairs Required | 950 Sq Ft

South Salem Vacation Rental w/ Furnished Deck!

10.0 out of 10, Exceptional, (2)
"Everything was easy and fine at the space. I had to stay for family reasons - so "location" was the most important factor to me. The worst thing in the unit is that the spiral stair is narrow - and a fat person or person with bad knees is NOT going to be using that stairwell easily. Otherwise, the unit had everything I needed and was perfectly appointed for an easy weekend stay. Enjoy!"
South Salem Vacation Rental w/ Furnished Deck!
Charming Mamaroneck Home ~ 22 Mi to Manhattan
Exterior

Charming Mamaroneck Home ~ 22 Mi to Manhattan

3.0 star property
6.0 out of 10, (1)
"Great quiet neighborhood, but this is only part of the home (1st floor, basement, and part of the 2nd floor) and the people upstairs are stepping loudly late into the night. The 3rd bathroom is in the basement with no shower curtain and a shower head that must be held during your entire shower. It was the 1 room that was actually dirty and I cleaned it before we used it. Internet info was inaccurate but provided when we requested. TV instructions lacking. Plenty of room for hanging out and...
Charming Mamaroneck Home ~ 22 Mi to Manhattan
New York Escape Near Times Square & Central Park!
Exterior

New York Escape Near Times Square & Central Park!

3.0 star property
New York Escape Near Times Square & Central Park!
Briarcliff Manor Estate w/ Hudson River Views
Living area

Briarcliff Manor Estate w/ Hudson River Views

3.0 star property
Briarcliff Manor Estate w/ Hudson River Views
Fairfield Cottage · Charming Fairfield Cottage By The Sea

Fairfield Cottage · Charming Fairfield Cottage By The Sea

10.0 out of 10, Exceptional, (31)
"What a wonderful find, and only an hour away from NYC. Fairfield CT is beautiful, friendly people, great restaurants, dog friendly, beautiful private beach, the list goes on and on. Thank you to Gerard for being so helpful, kind and always there to answer any questions, and give great recommendations. If you ever need a break from the city, this is the place to go to. Thanks again for such a wonderful holiday! We will be back."
Fairfield Cottage · Charming Fairfield Cottage By The Sea
Ridgefield Cottage: Walk to Town & Movie Theater!
Ridgefield Vacation Rental | 1BR | 1BA | 675 Sq Ft | Step-Free Access

Ridgefield Cottage: Walk to Town & Movie Theater!

Ridgefield Cottage: Walk to Town & Movie Theater!
Quiet Commack Cottage w/ Pool, 8 Mi to Beach!
Commack Vacation Rental | 3BR | 1BA | 1,300 Sq Ft | 3 Steps Required for Access

Quiet Commack Cottage w/ Pool, 8 Mi to Beach!

8.6 out of 10, Excellent, (4)
"We felt very cozy in the home. We were comfortable letting our dogs run around the back yard. Excellent location to all our favorite places. We will stay again. "
Quiet Commack Cottage w/ Pool, 8 Mi to Beach!
Secluded, private woodland cottage with two bedrooms and stone patio for summer!
Interior

Secluded, private woodland cottage with two bedrooms and stone patio for summer!

2.0 star property
Secluded, private woodland cottage with two bedrooms and stone patio for summer!
Charming 2 Bedroom Cottage in Peaceful New Canaan
Property grounds

Charming 2 Bedroom Cottage in Peaceful New Canaan

2.0 star property
10.0 out of 10, Exceptional, (2)
"The "Ice Cream Barn" is a beautifully modernized dwelling, situated on a lovely property of woods and fields. You really feel like you are experiencing what it's like to live in the delightful New England community of New Canaan. The hosts are most gracious and kind (another characteristic of NC). The space is relaxing, spacious, and charming, with plenty of outdoor space as well. Can't say enough about this terrific place."
Charming 2 Bedroom Cottage in Peaceful New Canaan
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

Stamford Suites
Property amenity

Stamford Suites

2.5 star property
6.8 out of 10, (772)
"It was in walking distance of the event we were going to."
The price is SAR 527
SAR 606 total
includes taxes & fees
14 Jan - 15 Jan
Stamford Suites
DUNE Fairfield Beach
Room

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 857
SAR 1,192 total
includes taxes & fees
5 Jan - 6 Jan
DUNE Fairfield Beach
Global Luxury Suites White Plains
Room

Global Luxury Suites White Plains

3.5 star property
6.8 out of 10, (27)
"Great location, friendly people, great apartment "
Global Luxury Suites White Plains
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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