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Compare 39 Cottages in Chappaqua with updated reviews, rates, and availability.

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Autumn Foliage - Private Patio View

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is SAR 631
SAR 935 total
includes taxes & fees
28 Dec - 29 Dec
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
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!
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
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

9.6 out of 10, Exceptional, (15)
"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
6 Jan - 7 January 2025
Cozy Cottage Getaway, Grill, Walk to Lake
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
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
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!
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
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 2,622 total
includes taxes & fees
27 Dec - 28 Dec
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
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.
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, (4)
"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
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
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, (1)
"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
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
Lakefront Brewster Vacation Rental w/ Private Dock
Property grounds

Lakefront Brewster Vacation Rental w/ Private Dock

3.0 star property
Lakefront Brewster Vacation Rental w/ Private Dock
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!
Updated Home w/ Patio Half Mile to West Point
Exterior

Updated Home w/ Patio Half Mile to West Point

3.0 star property
Updated Home w/ Patio Half Mile to West Point
Less than a mile from West Point! Lovely Cape Cod alongside a rolling brook.
Room

Less than a mile from West Point! Lovely Cape Cod alongside a rolling brook.

10.0 out of 10, Exceptional, (1)
"Ideal spot. Clean property. Cute house. Recently renovated."
Less than a mile from West Point! Lovely Cape Cod alongside a rolling brook.
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
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
3 Jan - 4 January 2025
Stamford Suites
Waterfront Retreat Center for Health & Wellness
Exterior

Waterfront Retreat Center for Health & Wellness

9.6 out of 10, Exceptional, (54)
"Second time our 24 person family group stayed here, and if anything, it was even better than last year! The location is exceptional, a quiet, private beautiful Victorian era house right on the Sound. The house is roomy, immaculate and very well equipped. Nancy is on top of everything and responds essentially immediately to any and every concern. There aren’t enough superlatives to describe our wonderful experience! "
Waterfront Retreat Center for Health & Wellness
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
Autumn Foliage - Private Patio View

Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands

9.8 out of 10, Exceptional, (105)
"Super cozy apartment with a beautiful view. Very welcoming host and a great place for a short stay near Bear Mountain. "
The price is SAR 631
SAR 935 total
includes taxes & fees
28 Dec - 29 Dec
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.

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