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Cottages in Pound Ridge

South Salem Vacation Rental w/ Furnished Deck!
Enjoy cooking in this well-equipped kitchen with a stove, oven, microwave, and sink.

South Salem Vacation Rental w/ Furnished Deck!

10.0 out of 10, Exceptional, (2)
"This was the second time I stayed at this property and really do love it. It is close enough to my family in Ridgefield for me to fee like I am just around the corner, while being in a quiet, peaceful private property. The setup was perfect for myself and my mom, but could also accommodate a larger group. It isn’t a big space, but had everything that we needed. I would highly recommend this property and will definitely be looking to stay here again on another visit. Thank you!"
South Salem Vacation Rental w/ Furnished Deck!
Westport "Gold Coast" across from Southport beach
Classic architecture with a black-framed window and lamp post.

Westport "Gold Coast" across from Southport beach

10.0 out of 10, Exceptional, (91)
"Fantastic place, location with great host. Highly recommended "
Westport "Gold Coast" across from Southport beach
Romantic retreat with stunning views of Croton River Gorge, a birder haven
Relax on the deck with a kayak nearby, surrounded by trees and a traditional building in the background.

Romantic retreat with stunning views of Croton River Gorge, a birder haven

9.8 out of 10, Exceptional, (6)
Romantic retreat with stunning views of Croton River Gorge, a birder haven
Second floor cottage apartment located in a private community.
Relax in this spacious living room with a large sofa, flat-screen TV, and pendant lights.

Second floor cottage apartment located in a private community.

9.6 out of 10, Exceptional, (16)
"Great time, nice little private neighborhood! Pretty views if you go for nice walks. 2 great parks near by. Lovely stay. Had everything we needed "
Second floor cottage apartment located in a private community.
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
Relax in a serene patio setting surrounded by lush greenery and a calm lake view.

Sweet Dotti's Cottage on Candlewood Lake - 60M NYC

9.6 out of 10, Exceptional, (14)
"Situated right on the lake. Easy to get to, nice working fireplace, lots of fun stuff for the kids and comfortable furniture. We really enjoyed our stay."
Sweet Dotti's Cottage on Candlewood Lake - 60M NYC
Walk to Beach: Luxe Home w/ Fire Pit in Rowayton!
House (3 Bedrooms) | Interior

Walk to Beach: Luxe Home w/ Fire Pit in Rowayton!

3.0 star property
Walk to Beach: Luxe Home w/ Fire Pit in Rowayton!
Adorable 1-Bedroom Cottage in Weston, CT
Enjoy cooking in this well-lit kitchen with a double oven, stainless steel sink, and white cabinetry.

Adorable 1-Bedroom Cottage in Weston, CT

10.0 out of 10, Exceptional, (42)
"Loved our stay. We'll be back I am sure."
$261 nightly
The price is $296
Aug 31 - Sep 1
Total includes taxes and fees
Adorable 1-Bedroom Cottage in Weston, CT
Lakefront Brewster Vacation Rental w/ Private Dock
Relax in this stylish living room with a high ceiling, sofa set, armchairs, and a coffee table, offering a view of the surrounding greenery.

Lakefront Brewster Vacation Rental w/ Private Dock

10.0 out of 10, Exceptional, (7)
"Felt relaxed from first step in the door! Wonderful view, comfortable beds, helpful management, great kitchen! Loved the heated tile floor in main bath! Lots of birds to enjoy with books and binoculars for identifying. "
Lakefront Brewster Vacation Rental w/ Private Dock
Hudson River Views + Firepit, Patio, Dog Run, Game Room Stone Manor
House (4 Bedrooms) | Interior

Hudson River Views + Firepit, Patio, Dog Run, Game Room Stone Manor

3.0 star property
Hudson River Views + Firepit, Patio, Dog Run, Game Room Stone Manor
Charming 2 Bedroom Cottage in Peaceful New Canaan
Enjoy serene views from this deck overlooking a well-maintained lawn and trees.

Charming 2 Bedroom Cottage in Peaceful New Canaan

2.0 star property
10.0 out of 10, Exceptional, (2)
"We had a wonderful Christmas getaway with family at the “Ice Cream Cottage”. It is much more spacious than it looks on the outside.It was clean and had everything we needed. Host was attentive to any questions we had.The fenced in yard was great for our “fur baby” to run around."
Charming 2 Bedroom Cottage in Peaceful New Canaan
Beachfront cottage located in the heart of Fairfield Beach!!
Enjoy a serene beach experience with access to the ocean and a scenic rocky shoreline.

Beachfront cottage located in the heart of Fairfield Beach!!

9.6 out of 10, Exceptional, (15)
"I grew up here! Always fun"
Beachfront cottage located in the heart of Fairfield Beach!!
Peaceful Cottage with Grill | Walk to Lake
Interior

Peaceful Cottage with Grill | Walk to Lake

9.8 out of 10, Exceptional, (19)
"This property was great. Clean, roomy and about 1/2 hour from West Point."
Peaceful Cottage with Grill | Walk to Lake
Trendy 1 bedroom +loft apartment w/ parking
Relax in this inviting living room with a comfortable sofa, flat-screen TV, and cozy rug.

Trendy 1 bedroom +loft apartment w/ parking

10.0 out of 10, Exceptional, (12)
"Perfect for my needs. Would stay again for sure"
Trendy 1 bedroom +loft apartment w/ parking
Serene Holmes Cottage Near Lakes & Trails!
Cottage (2 Bedrooms) | Front of property

Serene Holmes Cottage Near Lakes & Trails!

3.0 star property
Serene Holmes Cottage Near Lakes & Trails!
Beach house cottage steps to private beach in the heart of Bayville
Kitchen features a central island, stainless steel refrigerator, and white cabinetry.

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

10.0 out of 10, Exceptional, (10)
"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
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Surrounded by a serene snow-covered garden, this peaceful retreat offers a tranquil escape.

Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?

10.0 out of 10, Exceptional, (9)
"Wonderful stay!"
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Dreamy Hudson Valley Cottage w/ State Park Views
Relax in this spacious living room with a fireplace, comfortable seating, and a flat-screen TV.

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
Charming Fairfield Beach 3BR 2BA Cottage By The Sea
Dining

Charming Fairfield Beach 3BR 2BA Cottage By The Sea

10.0 out of 10, Exceptional, (32)
"Gerard was very responsive and helpful and the rental was lovely and in a great location. The beach access was great as were the beach accessories we could borrow! The house stayed nice and cool in during the hot days! Would stay again."
Charming Fairfield Beach 3BR 2BA Cottage By The Sea
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Relax in this inviting living room with a sofa, armchair, and woven coffee table, surrounded by natural elements and a large sliding glass door.

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

9.6 out of 10, Exceptional, (13)
"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."
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Summer Escape on Candlewood Lake – Private Beach, Hot Tub & Cozy Cottage!
Cozy bedroom with a bunk bed and single bed, featuring a flat-screen TV and air purifier.

Summer Escape on Candlewood Lake – Private Beach, Hot Tub & Cozy Cottage!

Summer Escape on Candlewood Lake – Private Beach, Hot Tub & Cozy Cottage!
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 Pound Ridge Hotel Reviews

Hotel NoMa, Trademark Collection by Wyndham

Hotel NoMa, Trademark Collection by Wyndham

10/10 Excellent
"Marie and her staff were super helpful! Kevin(server) was awesome! And good was delicious! Convient to train. Definitely would stay there again. Thank you. "
kim 2-night trip
Posted 2 days ago
Hotel NoMa, Trademark Collection by Wyndham