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Compare 264 Vacation Homes in Chappaqua with updated reviews, rates, and availability.

Lower Lvl Private 2BR/1BA Family/Pet Friendly
10.0 out of 10, Exceptional, (111)
"Property was perfect for our family. Gym, steam shower, and theatre room were all amazing. Effortless check in/check out process. Gorgeous home and neighborhood. Communication with our host Chris was easy and fast. Thank you for everything:) "
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
10.0 out of 10, Exceptional, (6)
"Absolutely loved our stay! The house was cozy, comfortable, and well-equipped. The host was responsive and made sure everything was just right. Highly recommend!!"
The price is SAR 1,872
SAR 3,437 total
includes taxes & fees
29 Sep - 30 Sep
Beautiful Escape! 'Parole LakeHouse' located 90min from NYC & 30min from Beacon
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
9.0 out of 10, Wonderful, (21)
"Loved it!! "
Charming 2 Bed backyard guesthouse close to Peekskill, WestPoint, & trails.
Ossining Vacation Rental Near River, Trails & MTA!
6.0 out of 10, (2)
"The house was nice & spacious. I do feel like it could use more seating in the living room, considering it can hold up to 11 guests. It would aslo be nice if there were tv's in the guest rooms upstairs. Also, maybe make sure the cleaning crew removes cobweks. "
Ossining Vacation Rental Near River, Trails & MTA!
Waterfront Retreat Center for Health & Wellness
9.6 out of 10, Exceptional, (52)
"I recently spent a couple of days celebrating my birthday with friends in this place, and it was an unforgettable experience. The house was beautifully furnished with a rich, wooden interior and stunning Tiffany stained glass windows. The expansive lawn offered breathtaking views of the bay, and the cozy pergola provided the perfect spot for relaxation. The elegant tableware added a touch of sophistication to our meals. Overall, it was a charming and memorable stay in a truly special...
Waterfront Retreat Center for Health & Wellness
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
10.0 out of 10, Exceptional, (71)
"Hoyse is in a beautiful location and was very clean. The host was responsive and helpful. I would give it 5 stars if it actually had 3 bedrooms."
Privacy in the hills one hour from NYC and minutes to Breakneck Mtn.
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
9.2 out of 10, Wonderful, (12)
"Our stay was really amazing, the deck out back with the grill, trees and big space really helped with end of day peace. "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Modern And Quiet Getaway
9.8 out of 10, Exceptional, (21)
"We had a great stay. Host was super friendly. Room was just as pictured and advertised. Quick Metro train available to get into the city in 30 minutes. Apartment was clean and there were all the things needed to cook if needed. Lovely home beautiful kept yard. Nice quiet neighborhood. 5 minute car or taxi ride to train station with ample parking available. We would recommended it! Thanks to the host for all the information provided. Lucio and Pilar"
Modern And Quiet Getaway
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury
9.2 out of 10, Wonderful, (7)
"Super well-appointed house with everything we needed for our stay. Hosts were easy to communicate with and responded very quickly."
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
10.0 out of 10, Exceptional, (87)
"Excellent! Loved it! Home was more spacious than we ever thought. The rooms had so much character! Beautiful yard. Perfect setting. We would stay here again."
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
10.0 out of 10, Exceptional, (19)
"The house is great. Well designed. Top line appliances. Views wonderful. Only negative is a stretch of the access road that is hard dirt and loose stone. Keeps out the riff raff, I guess."
'The Glabin’: Garrison Gem w/ Deck & Fire Pit!
Upstate group-sized home in Putnam Valley, 15 minutes from Cold Spring, NY
10.0 out of 10, Exceptional, (7)
"My family wanted a quiet place to stay for a few days. We did some local hiking and sightseeing. The architecture of the house is gorgeous. There were plenty of places to relax both inside and out."
Upstate group-sized home in Putnam Valley, 15 minutes from Cold Spring, NY
Quaint duplex with private yard. Walk to beach, dining, & shopping!
10.0 out of 10, Exceptional, (35)
"Needed a place to stay with our dog while visiting our granddaughters in a nearby town."
Quaint duplex with private yard. Walk to beach, dining, & shopping!
Charming Apartment in Quiet Neighborhood
10.0 out of 10, Exceptional, (13)
"Had a peaceful stay here for 2 nights. A lovely oasis, it has everything you could possibly need … and more! Quiet, clean, newly renovated, and gracious and helpful hosts. I’ll definitely stay here again when I come back to the area. "
Charming Apartment in Quiet Neighborhood
West Point Modern 3 bed 2 bath house with Hot Tub, BBQ, Fire Pit and more!
10.0 out of 10, Exceptional, (3)
"Four night stay with my adult sons and grandson. The owner went above and beyond expectations in making this a great choice. Timely communication, picture and written description accurate, The deck and furnishings are an added bonus along with the hot tub. Three or four types of coffee makers. Coffee, tea and drinks provided. Each bedroom has a large TV that eliminated arguments over which game we would watch. Walking distance to the West Point Museum, Visitor Center and Main...
West Point Modern 3 bed 2 bath house with Hot Tub, BBQ, Fire Pit and more!
Modern, Magical Woodsy Escape 1 Hour From NYC
10.0 out of 10, Exceptional, (12)
"Every two to three years we take the whole family on a getaway vacation. This trip was a change of pace from the previous ones - Disney, Canadian Rockies - and it was PERFECT. The house was perfect for the size of our family, and the ambiance could not have been better. The s'mores on the last night overthe fire pit in the back yard was a fitting conclusion to a marvelous long weekend. "
Modern, Magical Woodsy Escape 1 Hour From NYC
Amazing Oasis Near NYC
2.0 star property
6.0 out of 10, (1)
"The property was clean and communication from the host was good. The “Oasis” did not match the full description. There were flaws like loose doorknobs. There was not a bed in 3rd bedroom. There were missing light bulbs in one lamp. The kitchen is barely equipped. The location was good for what we needed. "
Amazing Oasis Near NYC
Historic Connecticut Home w/ Grill & Spacious Yard
10.0 out of 10, Exceptional, (2)
"House is even cooler than the pictures give it credit for. Beautiful and funky. We really enjoyed our stay!!"
Historic Connecticut Home w/ Grill & Spacious Yard
Waterfront Lake House. Near NYC and hiking trials. Complimentary kayaks provided
2.0 star property
10.0 out of 10, Exceptional, (1)
"It is a small property but an excellent location on the lake. Kayaks and paddle boat provided were an added bonus. Owner is very responsive and helpful. Kitchen could be better equipped. Overall a very pleasant and enjoyable stay."
Waterfront Lake House. Near NYC and hiking trials. Complimentary kayaks provided
2 mini-bedrooms apartment with antique bathtub.
10.0 out of 10, Exceptional, (18)
"Conveniently located to small downtown area & train into NYC. "
2 mini-bedrooms apartment with antique bathtub.
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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
2.5 star property
6.8 out of 10, (746)
"It was more than i expected. "
The price is SAR 571
SAR 640 total
includes taxes & fees
5 Oct - 6 Oct
Stamford Suites
Waterfront Retreat Center for Health & Wellness
9.6 out of 10, Exceptional, (52)
"I recently spent a couple of days celebrating my birthday with friends in this place, and it was an unforgettable experience. The house was beautifully furnished with a rich, wooden interior and stunning Tiffany stained glass windows. The expansive lawn offered breathtaking views of the bay, and the cozy pergola provided the perfect spot for relaxation. The elegant tableware added a touch of sophistication to our meals. Overall, it was a charming and memorable stay in a truly special...
Waterfront Retreat Center for Health & Wellness
Serene Mountain Top Views overlooking Hudson River and Surrounding Highlands
9.8 out of 10, Exceptional, (99)
"Wonderful hilltop location. Beautiful view. Nice apartment. Great hosts. Wish we could have stayed longer! "
The price is SAR 653
SAR 961 total
includes taxes & fees
2 Oct - 3 Oct
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.