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Compare 47 Cottages in Chappaqua with updated reviews, rates, and availability.

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (109)
"Great place and host!"
The price is SARĀ 630
SARĀ 1,044 total
includes taxes & fees
4 May - 5 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

Trendy 1 bedroom +loft apartment w/ parking

10.0 out of 10, Exceptional, (9)
"We really enjoyed this place and location. Everything as advertised. Clean, safe area with great parking, convenient to 95 and all of Stamford, comfortable bed, W/D steps away. "
Trendy 1 bedroom +loft apartment w/ parking

Cos Cob Cottage- Full Kitchen, Pet Friendly

10.0 out of 10, Exceptional, (3)
"Great Property. Driveway parking a bit of a challenge"
Cos Cob Cottage- Full Kitchen, Pet Friendly

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

Beautiful Cottage in Hudson Valley w/Pool & Views

10.0 out of 10, Exceptional, (11)
"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."
Beautiful Cottage in Hudson Valley w/Pool & Views

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 ā€œIce Cream Cottageā€. 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 ā€œfur babyā€ to run around."
Charming 2 Bedroom Cottage in Peaceful New Canaan

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!

Lakefront Brewster Vacation Rental w/ Private Dock

10.0 out of 10, Exceptional, (5)
"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

Dreamy Hudson Valley Cottage w/ State Park Views

9.6 out of 10, Exceptional, (14)
"We loved our two nights at this perfect, comfortable cottage in the Garrison woods. Communication with Ashley was terrific, very prompt and welcoming. The house was very clean and we had a great view. Thank you for a great stay! "
Dreamy Hudson Valley Cottage w/ State Park Views

This cottage is a 2 bedroom(s), 1 bathrooms, located in Putnam Valley, NY.

9.8 out of 10, Exceptional, (17)
"Really nice little cabin in Putnam, close to cold spring and beacon. Cozy and enjoyed the stay. Beds were very comfortable and place was very clean."
This cottage is a 2 bedroom(s), 1 bathrooms, located in Putnam Valley, NY.

Second floor cottage apartment located in a private community.

9.6 out of 10, Exceptional, (15)
"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.

Ridgefield Cottage: Walk to Town & Movie Theater!

Ridgefield Cottage: Walk to Town & Movie Theater!

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

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

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

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

Updated Home w/ Patio Half Mile to West Point

3.0 star property
Updated Home w/ Patio Half Mile to West Point

Lakefront Brewster Vacation Rental w/ Private Dock

3.0 star property
Lakefront Brewster Vacation Rental w/ Private Dock

Charming Highland Falls Home < 2 Mi to West Point!

3.0 star property
Charming Highland Falls Home < 2 Mi to West Point!

3 Mi to Downtown: Spacious White Plains Home

3.0 star property
3 Mi to Downtown: Spacious White Plains Home
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 Chappaqua

Stamford Suites

3.0 star property
6.0 out of 10, (29)
"Convenience. Full kitchen and spacious rooms"
The price is SARĀ 750
SARĀ 863 total
includes taxes & fees
16 May - 17 May
Stamford Suites

Global Luxury Suites White Plains

3.5 star property
6.6 out of 10, (30)
"Nice view from the apartment and great for business trip. "
Global Luxury Suites White Plains

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (109)
"Great place and host!"
The price is SARĀ 630
SARĀ 1,044 total
includes taxes & fees
4 May - 5 May
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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.