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Chappaqua Vacation Rentals

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Chappaqua vacation rentals

A hallway with hardwood flooring, a staircase, and a dining area with a chair and table.

1. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
3.0 star property
Ossining
The price is AED 1,062
AED 3,059 total
includes taxes & fees
21 Oct - 22 Oct
Snow Days & City Escapes: Spacious Ossining Home
A modern kitchen with white cabinets, a stainless steel dishwasher, a black granite countertop, and a window with a view of trees.

2. Snow Days & City Escapes: Spacious Ossining Home

Snow Days & City Escapes: Spacious Ossining Home
Ossining
8.2 out of 10, Very good, (19 reviews)
"A family trip with teens and tweens- a perfect space! Clean, hist was friendly, the house was stocked with all we'd need! A great getaway for any family NYC trip!"
United States
Justeen P.
The price is AED 859
AED 3,093 total
includes taxes & fees
21 Oct - 22 Oct
Snow Days & City Escapes: Spacious Ossining Home
A stone staircase leading to a house with a stone wall and a metal gate.

3. Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.

Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
Croton-on-Hudson
9.6 out of 10, Exceptional, (24 reviews)
"A lovely spot, very nice accommodations.Breakfast supples thoughtfully supplied as well as champagne to enjoy. "
United States
Eva C.
The price is AED 918
AED 1,563 total
includes taxes & fees
5 Oct - 6 Oct
Fall colors HQs.Fish, kayak and bird watch at Croton River Gorge.
A neatly made bed with a black and white duvet, a wooden headboard, and a bedside table with a lamp. There are three framed artworks on the wall above the bed.

4. 'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway

'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
Croton-on-Hudson
10.0 out of 10, Exceptional, (3 reviews)
"Great stay!"
United States
Ann S.
The price is AED 547
AED 1,112 total
includes taxes & fees
18 Oct - 19 Oct
'Croton Nook' - Spacious Studio with Full Eat-in Kitchen, Cozy Getaway
A dining table set with plates, cutlery, and glasses, with a bowl of fruit and a wine glass in the background.

5. Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food

Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
CROTON HDSN
9.8 out of 10, Exceptional, (93 reviews)
"Our stay was just perfect! We chose the location based on being close-ish to family in northern Westchester and friends in the city and it was perfect. Maria is an excellent host and super attentive and helpful when needed. The apartment was the perfect size for our family and super cozy after a long day. We'd definitely stay again!"
United States
Aimee S.
The price is AED 591
AED 1,238 total
includes taxes & fees
5 Oct - 6 Oct
Comfortable 2bd - Convenience & Style - 45min to NYC - Great Food
A hotel room with a bed, a desk, a chair, a TV, and a window with a curtain.

6. 1 Queen Bed | Smoking

1 Queen Bed | Smoking
Elmsford
10.0 out of 10, Exceptional, (1 review)
"Beds were adequate, nothing special but perfectly fine for a short overnight stay."
United States
Anonymous traveler
The price is AED 450
AED 515 total
includes taxes & fees
7 Oct - 8 Oct
1 Queen Bed | Smoking
A modern living room with a stone fireplace, a leather sofa, a yellow armchair, a flat-screen TV, and a bookshelf.

7. 'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!

'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
Croton-on-Hudson
10.0 out of 10, Exceptional, (9 reviews)
"We had an extended stay at Croton Quarters, it was great! The hosts truly are pet-friendly, the location is ideal, and the property comfortable for a longer term visit. "
United States
Mateo A.
The price is AED 833
AED 1,562 total
includes taxes & fees
11 Oct - 12 Oct
'Croton Quarters' - Comfortable Apt with Modern Amenities near Food, NYC Close!
An outdoor dining area with tables set for a formal event, featuring candles, glassware, and floral centerpieces.

8. Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!

Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
Ossining
8.8 out of 10, Excellent, (10 reviews)
"Super fun location! Host was very helpful. The house is very comfortable for large groups "
United States
natalie l.
The price is AED 1,873
AED 3,661 total
includes taxes & fees
5 Oct - 6 Oct
Castle Retreat w/ Pool, BBQ, Game Room & Pets OK!
A campfire with a wooden table and benches by a lake.

9. 2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (43 reviews)
"Nice stay"
United States
Christopher J.
The price is AED 595
AED 1,143 total
includes taxes & fees
7 Oct - 8 Oct
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
The Stamford Suites Hotel entrance with a clear view of the building's facade, a large sign, and a parking area.

10. Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.4 out of 10, (186 reviews)
"Very friendly staff and nice clean hotel!!"
United States
Alice
The price is AED 567
AED 652 total
includes taxes & fees
11 Oct - 12 Oct
Stamford Suites
A spacious living room with a large window, a ceiling fan, a dining area with a table and chairs, and a staircase leading to an upper level.

11. Summer Pool Oasis Custom Bar Arcade Pool Table

Summer Pool Oasis Custom Bar Arcade Pool Table
2.0 star property
Ossining
The price is AED 2,219
AED 4,305 total
includes taxes & fees
3 Nov - 4 Nov
Summer Pool Oasis Custom Bar Arcade Pool Table
A garden with a stone wall, a wooden fence, and a gravel path.

12. Piermont Oasis

Piermont Oasis
Piermont
9.6 out of 10, Exceptional, (22 reviews)
"Great place to stay! "
United States
Megan D.
The price is AED 441
AED 773 total
includes taxes & fees
3 Nov - 4 Nov
Piermont Oasis
A kitchenette with a water dispenser, microwave, coffee machine, and a snack vending machine.

13. 2 Full Beds | Non-Smoking

2 Full Beds | Non-Smoking
Elmsford
10.0 out of 10, Exceptional, (1 review)
"The staff were attentive without being pushy, and the bed provided good comfort."
United States
Anonymous traveler
The price is AED 508
AED 580 total
includes taxes & fees
5 Oct - 6 Oct
2 Full Beds | Non-Smoking
A motel with a blue awning and a '6 Now Open' sign.

14. 1 Queen Bed | Non-Smoking

1 Queen Bed | Non-Smoking
Elmsford
10.0 out of 10, Exceptional, (3 reviews)
"Short trip so just needed something quick, location near Westchester Airport suited us well."
United States
Anonymous traveler
The price is AED 472
AED 539 total
includes taxes & fees
7 Oct - 8 Oct
1 Queen Bed | Non-Smoking
A modern hotel lobby with a stone wall, a coffee machine, a refrigerator, and a sign advertising a motel.

15. 1 King Bed | Non-Smoking

1 King Bed | Non-Smoking
Elmsford
10.0 out of 10, Exceptional, (2 reviews)
"Our rooms felt cozy enough for two people with decent privacy due to separate bathrooms nearby too.The location suited our plan moving between airport runs & visits close by malls perfectly."
United States
Anonymous traveler
The price is AED 482
AED 552 total
includes taxes & fees
7 Oct - 8 Oct
1 King Bed | Non-Smoking
A bedroom with a large bed, a black sofa, a mirror, and a chandelier.

16. Nice Cozy Room By Empire City Casino And Cross County Shopping Center

Nice Cozy Room By Empire City Casino And Cross County Shopping Center
Southeast Yonkers
7.8 out of 10, Good, (19 reviews)
"Great location"
United States
Jordan S.
The price is AED 347
AED 495 total
includes taxes & fees
5 Oct - 6 Oct
Nice Cozy Room By Empire City Casino And Cross County Shopping Center
A covered area with exercise equipment, chairs, and a view through large windows.

17. 1BR Queen near NYC | Trails, Biking & Sauna Bliss

1BR Queen near NYC | Trails, Biking & Sauna Bliss
Ossining
The price is AED 942
AED 1,185 total
includes taxes & fees
1 Nov - 2 Nov
1BR Queen near NYC | Trails, Biking & Sauna Bliss
A modern kitchen with white cabinets, a wooden countertop, and a refrigerator.

18. Quiet Apt with Coffee Bar, 1/2 Mile to West Point!

Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
Highland Falls
9.4 out of 10, Exceptional, (24 reviews)
"Exactly what we needed for two people prior to an early morning touring West Point. "
United States
Andrew L.
The price is AED 422
AED 1,127 total
includes taxes & fees
5 Oct - 6 Oct
Quiet Apt with Coffee Bar, 1/2 Mile to West Point!
A modern living room with a sofa, a coffee table, and a bar stool.

19. Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
Downtown Stamford
9.2 out of 10, Wonderful, (11 reviews)
"loved walking the city. pizza was good."
United States
michelle b.
The price is AED 588
AED 1,227 total
includes taxes & fees
18 Oct - 19 Oct
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!
A compact room with a kitchenette, a bed, a wall decorated with photos and a mirror, and a 'No Fishing From Bridge' sign.

20. Welcome to Sweet Abby Rose!

Welcome to Sweet Abby Rose!
Brewster
10.0 out of 10, Exceptional, (1 review)
"The place is super comfortable and has a great outdoor area for chatting; I would definitely like to come back and stay longer."
United States
Yasmin G.
The price is AED 367
AED 681 total
includes taxes & fees
11 Oct - 12 Oct
Welcome to Sweet Abby Rose!
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 Chappaqua Hotel Reviews

Royal Regency Hotel

Royal Regency Hotel

10/10 Excellent
"Michael & Lauren, front desk attendants were so helpful and amazing. We asked to change to other rooms and they were so accommodating. The layout of the bathroom/living area was strange as there was sliding glass doors that allowed you to see from the bathroom into the sleeping area but they were a very cool design & the kids really enjoyed it. The hotel rooms were clean and everything was good. The breakfast was fresh and a very nice spread. The kids enjoyed the mini donuts. the staff in the breakfast area were so kind and sweet. The onsite restaurant food was very good and the atmosphere was pleasant. Our waitress was very friendly and helpful with helping us decide what to order."
Catharina 5-night trip
Posted 1 hour ago
Royal Regency Hotel

Frequently asked questions

Can I find a vacation rental in Chappaqua?

Yes, we offer vacation rentals in Chappaqua near Chappaqua Performing Arts Center, or you can select a more secluded option if you want a relaxing stay. Our travelers say Chappaqua has a good selection of restaurants. Make sure you have time to check out the sporting events and entertainment choices during your trip.

What are some of the best vacation home rentals in Chappaqua?

Modern Luxury Home w GameRoom & Parking: You might like this vacation home rental near Chappaqua. It is situated near the airport and has a rooftop terrace and free WiFi to help you feel content during your stay. It has 3 bedrooms as well as a kitchen with a full-sized fridge, a dishwasher, and a stovetop, so you can cook with friends or family.

How many vacation rentals will I find in Chappaqua?

Expedia has 3 vacation rentals for your stay in Chappaqua.

What’s there to see and do in Chappaqua?

Explore the area and family-friendly sights such as Bruce Museum of Arts and Science, or get out into nature at a spot like Hardscrabble Wilderness Area. Chappaqua Performing Arts Center and Rockefeller State Park Preserve are a couple of places you'll find in the larger area.

What’s a vacation rental in Chappaqua like?

Vacation rentals are privately owned properties you can stay in for several days or longer in Chappaqua. Vacation rentals offer extras like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, vacation rentals can provide a sense of seclusion away from shared hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a great option for a family getaway.