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Next weekend
3 Oct - 5 Oct
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10 Oct - 12 Oct
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24 Oct - 26 Oct
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21 Nov - 23 Nov

Featured Cottages in Pound Ridge

Our top choices for Pound Ridge cottages

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Property grounds

Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven

9.8 out of 10, Exceptional, (7)
"We loved our stay at the Carriage House. Patrick and Kathryn were wonderful hosts. They provided information in a timely manner, and were quick to respond to any questions. Our accommodations were clean, comfortable and well appointed, and Patrick and Kathryn included truly thoughtful touches. The location was perfect for exploring Croton-on-Hudson and the Hudson Valley. We'd love to come back!"
Fall Colors HQs. Stunning views of Croton River Gorge, a birder haven
Cos Cob Cottage- Full Kitchen, Pet Friendly
Exterior

Cos Cob Cottage- Full Kitchen, Pet Friendly

10.0 out of 10, Exceptional, (4)
"2 night stay over Thanksgiving holiday. Cozy Cottage was just lovely. Fully applianced and stocked kitchen. Large bathroom-super soft towels. King size bed was comfy and cozy. Living room was perfect for relaxing. Rules clearly communicated. Owners were very helpful and responsive. Driveway a little tricky to maneuver when parking spots are occupied. Safe location…. Good walking and exploring in the area "
Cos Cob Cottage- Full Kitchen, Pet Friendly
Westport "Gold Coast" across from Southport beach
Exterior

Westport "Gold Coast" across from Southport beach

10.0 out of 10, Exceptional, (92)
"Easy communication, clean apartment, good location for beach and nearby towns. "
Westport "Gold Coast" across from Southport beach
Peaceful Cottage with Grill | Walk to Lake
Exterior

Peaceful Cottage with Grill | Walk to Lake

9.8 out of 10, Exceptional, (21)
"This property was great. Clean, roomy and about 1/2 hour from West Point."
Peaceful Cottage with Grill | Walk to Lake
Second floor cottage apartment located in a private community.
Exterior

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

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?
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Fridge, microwave, oven, stovetop

Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT

10.0 out of 10, Exceptional, (8)
"Great relaxing stay quite and comfortable "
Tranquil 1 bedroom cottage with King size bed & Fireplace in charming Bethel, CT
Charming Studio-Cottage with WiFi & TV free parking in Greenwich
Exterior

Charming Studio-Cottage with WiFi & TV free parking in Greenwich

Charming Studio-Cottage with WiFi & TV free parking in Greenwich
Trendy 1 bedroom +loft apartment w/ parking
Smart TV

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
Lakefront Brewster Vacation Rental w/ Private Dock
Cottage (3 Bedrooms) | Interior

Lakefront Brewster Vacation Rental w/ Private Dock

3.0 star property
Lakefront Brewster Vacation Rental w/ Private Dock
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
Property grounds

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

2.0 star property
10.0 out of 10, Exceptional, (3)
"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 - Pet Friendly!
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!
Dreamy Hudson Valley Cottage w/ State Park Views
Interior

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
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, (18)
"I grew up here! Always fun"
Beachfront cottage located in the heart of Fairfield Beach!!
Beach house cottage steps to private beach in the heart of Bayville
Exterior

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
New Fairfield Vacation Rental w/ Lake Views!
Property grounds

New Fairfield Vacation Rental w/ Lake Views!

3.0 star property
New Fairfield Vacation Rental w/ Lake Views!
Charming Fairfield Beach 3BR 2BA Cottage By The Sea
Outdoor dining

Charming Fairfield Beach 3BR 2BA Cottage By The Sea

10.0 out of 10, Exceptional, (33)
"Clean, quaint spot for a family gathering. A little chilly in February but very calming and pleasant stay."
Charming Fairfield Beach 3BR 2BA Cottage By The Sea
Sun and Fun on the beach!!
Outdoor dining

Sun and Fun on the beach!!

9.6 out of 10, Exceptional, (17)
"Perfect beach and outdoor life for young kids! Such a great relaxing long weekend - the house had everything we needed. Hoping for another stay soon!"
Sun and Fun on the beach!!
Cozy Retreat w/ Pool, Cinema Room & Fire Pit
Outdoor dining

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!
Exterior

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

10.0 out of 10, Exceptional, (1)
"Lovely little 2/2 house in a great location with just about everything we needed. Very quiet too. Our host, Jonathan was very responsive when we had questions or concerns. We would highly recommend!"
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

Norwalk Inn & Conference Center

Norwalk Inn & Conference Center

10/10 Excellent
"The property is clean, the bed - comfortable, the staff - friendly. What more could you ask for? Everything was great! "
Jane 2-night trip
Posted 3 days ago
Norwalk Inn & Conference Center

Find out more about Pound Ridge

Find out more about Pound Ridge

Pound Ridge Cottages information

Number of reviews
248
Accommodation
57 Cottages
Lowest Price
Highest Price

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