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Compare 50 Cottages in Pound Ridge with updated reviews, rates, and availability.

Putnam Valley Vacation Rental: Patio & Lake Views!
Putnam Valley Vacation Rental | 3BR | 2BA | 7 Steps Required to Enter
Putnam Valley Vacation Rental: Patio & Lake Views!
9.8 out of 10, Exceptional, (11)
"Cozy, clean property. We had everything we needed for a 3-night stay for West Point Family Weekend. Several stores & restaurants conveniently nearby. Host Neury was most accommodating. Incredible views & scenery!!"
Putnam Valley Vacation Rental: Patio & Lake Views!
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Living area
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
10.0 out of 10, Exceptional, (5)
"We had a wonderful stay and this house did not disappoint! The home is very well appointed and has everything you need. Property is very clean and would recommend this home to anyone visiting this area. Will definitely be coming back!"
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
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
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
Property grounds
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
9.6 out of 10, Exceptional, (14)
"Landscaping was spectacular and we enjoyed a beautiful view of the lake. Baths and bedrooms very clean. Plenty of charging ports. Terrible mold and mildew smell in lower level. Number of hazards noted, handrail missing on stairs, no lights on outdoor stairway, thermostat access by leaning over the stairs. The property needs a good deep cleaning."
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
Trendy 1 bedroom +loft apartment w/ parking
Interior
Trendy 1 bedroom +loft apartment w/ parking
10.0 out of 10, Exceptional, (4)
"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
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
Putnam Valley Vacation Rental: Patio & Lake Views!
Terrace/patio
Putnam Valley Vacation Rental: Patio & Lake Views!
3.0 star property
Putnam Valley Vacation Rental: Patio & Lake Views!
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, (33)
"This cottage is so beautiful, well equipped and comfortable. The hosts were welcoming, accommodating and checked in with us to make certain we were enjoying our visit. The gorgeous location was perfect for us. We were visiting family in the area which is why we chose it. We didn’t realize how near it was to quaint towns, great restaurants, etc. We also spent an afternoon at nearby Sherwood Island followed by lobster rolls at a nearby restaurant. Thank you! Looking forward to a return visit! "
The price is SAR 732
SAR 1,139 total
includes taxes & fees
17 Nov - 18 Nov
Adorable 1-Bedroom Cottage in Weston, CT
Westport "Gold Coast" across from Southport beach
Property grounds
Westport "Gold Coast" across from Southport beach
10.0 out of 10, Exceptional, (82)
"Had the best time. Walked to the beach. Great local restaurants as well."
Westport "Gold Coast" across from Southport beach
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
Cozy Cottage Getaway, Grill, Walk to Lake
Enjoy the morning sunlight streaming through the windows while staying cozy inside. Pull down filter shades on all windows for privacy. (Use of fireplace is not allowed unfortunately!)
Cozy Cottage Getaway, Grill, Walk to Lake
10.0 out of 10, Exceptional, (14)
"My husband and I were very happy with our stay here. Sara was a communicative and flexible host, even before we arrived. The place matched our expectations from the listing. The cottage was clean, comfortable and had everything we needed for our multiple day stay. "
The price is SAR 649
SAR 1,515 total
includes taxes & fees
2 Dec - 3 Dec
Cozy Cottage Getaway, Grill, Walk to Lake
Beautiful Cottage in Hudson Valley w/Pool & Views
Interior
Beautiful Cottage in Hudson Valley w/Pool & Views
9.8 out of 10, Exceptional, (10)
"The house was exactly as advertised. It was clean, well maintained and comfortable! The location was beautiful and private yet close to nearby stores and activities."
The price is SAR 1,127
SAR 2,621 total
includes taxes & fees
20 Nov - 21 Nov
Beautiful Cottage in Hudson Valley w/Pool & Views
Dreamy Hudson Valley Cottage w/ State Park Views
Garrison Vacation Rental | 1BR | 1BA | 650 Sq Ft | Steps Required
Dreamy Hudson Valley Cottage w/ State Park Views
9.8 out of 10, Exceptional, (11)
"Absolutely gorgeous house! Great location and a beautiful view from the porch. Would highly recommend to anyone. "
Dreamy Hudson Valley Cottage w/ State Park Views
🔥Fairfield County Cozy cottage , super close great adventure
Living area
🔥Fairfield County Cozy cottage , super close great adventure
9.8 out of 10, Exceptional, (6)
"Comfortable house, not huge, but nicely decorated. Host was very quick to respond when I had trouble with door code. The only con for us was lack of handrails on steps to exterior doors (front and back). Otherwise a great place to stay."
🔥Fairfield County Cozy cottage , super close great adventure
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!!
Lakefront Brewster Vacation Rental w/ Private Dock
Brewster Vacation Rental | 3BR | 2BA | Stairs Required | 2,600 Sq Ft
Lakefront Brewster Vacation Rental w/ Private Dock
10.0 out of 10, Exceptional, (3)
"Family trip consisting of 2 grandparents, 2 parents, and 1 adult grandchild went off without a hitch. The property is so beautiful- meticulously clean house, soft beds and luxury bedding, top notch kitchen appliances, with the most peaceful view of the lake. Excellent communication from host, including helpful welcome book. Fresh loaf of cranberry bread from local farmer’s market was a nice touch. DeCicco’s Market was our go-to for groceries / wish we had one of those at home. Enjoyed...
Lakefront Brewster Vacation Rental w/ Private Dock
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, (1)
"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
Dreamy Hudson Valley Cottage w/ State Park Views
Living area
Dreamy Hudson Valley Cottage w/ State Park Views
3.0 star property
10.0 out of 10, Exceptional, (1)
"The house was amazing with great amenities. The kitchen was stocked with all the utensils and cutlery. The patio was a good addition. Overall great stay! "
Dreamy Hudson Valley Cottage w/ State Park Views
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!!
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 Pound Ridge

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
Stamford Suites
Property amenity
Stamford Suites
2.5 star property
6.8 out of 10, (764)
"The room was nice and clean. The staff was friendly and there are lots of food choices near by. "
The price is SAR 540
SAR 604 total
includes taxes & fees
26 Nov - 27 Nov
Stamford Suites
DUNE Fairfield Beach
Room
DUNE Fairfield Beach
3.0 star property
9.0 out of 10, Wonderful, (41)
"The property is generally old, but it was a nice renovation. Of the room. "
The price is SAR 958
SAR 1,448 total
includes taxes & fees
21 Nov - 22 Nov
DUNE Fairfield 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.

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