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Chappaqua Vacation Rentals

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Our top choices for Chappaqua vacation rentals

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border
Historic District
10.0 out of 10, Exceptional, (12 reviews)
"This house was so lovely, clean, cozy, and well-appointed - everything we could have asked for for a girls' weekend! And so close to the town of Westport with its excellent restaurants and shops. The best!"
United States
Rebecca H.
$758 nightly
The price is $860
Jul 13 - Jul 14
Total with taxes and fees
Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
$348 nightly
The price is $400
Jul 5 - Jul 6
Total with taxes and fees
Guesthouse at Norwalk Inn

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment
Historic District
10.0 out of 10, Exceptional, (1 review)
"Great "
United States
Ricky W.
$341 nightly
The price is $386
Jul 1 - Jul 2
Total with taxes and fees
King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

Spacious Retreat with Game Room and Fire Pit

Spacious Retreat with Game Room and Fire Pit
West Norwalk
$692 nightly
The price is $784
Jun 24 - Jun 25
Total with taxes and fees
Spacious Retreat with Game Room and Fire Pit

Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach
Cove - East Side - Shippan
9.2 out of 10, Wonderful, (25 reviews)
"House was amazing, with a wonderful view. Hosts were responsive and helpful. Will need to come back in summer!"
United States
Scott H.
$893 nightly
The price is $948
Jun 19 - Jun 20
Total with taxes and fees
Waterview House Walking Distance from Cove Beach

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Spacious 3 Bd Home Pet Friendly, Parking and Laundry
Cove - East Side - Shippan
8.0 out of 10, Very Good, (6 reviews)
"the home was nice clean if in the area I would stay here again"
United States
james w.
$624 nightly
The price is $680
Jun 28 - Jun 29
Total with taxes and fees
Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Stamford Hideaway w/ Fire Pit

Stamford Hideaway w/ Fire Pit
Cove - East Side - Shippan
$322 nightly
The price is $364
Jul 8 - Jul 9
Total with taxes and fees
Stamford Hideaway w/ Fire Pit

New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (24 reviews)
"Excellent home, met all expectations, and attentive staff"
United States
Steve G.
New Beach Home near Stamford Downtown/Shippan

Stylish Home With Free ParkingZA

Stylish Home With Free ParkingZA
Glenbrook-Belltown
$415 nightly
The price is $470
Jun 22 - Jun 23
Total with taxes and fees
Stylish Home With Free ParkingZA

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

Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
New Canaan
10.0 out of 10, Exceptional, (6 reviews)
"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."
United States
danyelle s.
$632 nightly
The price is $717
Jun 24 - Jun 25
Total with taxes and fees
Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!

Stylish Home and Cozy

Stylish Home and Cozy
Downtown Stamford
$354 nightly
The price is $401
Jun 18 - Jun 19
Total with taxes and fees
Stylish Home and Cozy

Stylish Home with Free Parking

Stylish Home with Free Parking
Downtown Stamford
$264 nightly
The price is $299
Jun 16 - Jun 17
Total with taxes and fees
Stylish Home with Free Parking

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.6 out of 10, (127 reviews)
"Great location, friendly and helpful staff. Good value for money."
United States
ian
$136 nightly
The price is $156
Jun 22 - Jun 23
Total with taxes and fees
Stamford Suites

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)
"Perfect apartment and location. Amazing communication. Thank you!!"
United States
Ryan F.
$277 nightly
The price is $314
Jun 28 - Jun 29
Total with taxes and fees
Luxury 1BR Apartment in Downtown Stamford w/ Amenities & Easy Access to NYC!

Modern Luxe 1BR Apt in Downtown Stamford

Modern Luxe 1BR Apt in Downtown Stamford
Downtown Stamford
9.6 out of 10, Exceptional, (5 reviews)
"Our family stayed in the hotel(s) next door. It was so nice to have our own personal space!"
United States
Jill G.
$386 nightly
The price is $437
Jul 4 - Jul 5
Total with taxes and fees
Modern Luxe 1BR Apt in Downtown Stamford

The Gallery in Downtown Stamford

The Gallery in Downtown Stamford
Downtown Stamford
10.0 out of 10, Exceptional, (5 reviews)
"Great location in Downtown Stamford. "
United States
Jim W.
$584 nightly
The price is $661
Jun 20 - Jun 21
Total with taxes and fees
The Gallery in Downtown Stamford

Solara – Luxury 1BR Downtown

Solara – Luxury 1BR Downtown
Downtown Stamford
$377 nightly
The price is $427
Jun 18 - Jun 19
Total with taxes and fees
Solara – Luxury 1BR Downtown

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
9.8 out of 10, Exceptional, (15 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
$353 nightly
The price is $399
Jun 18 - Jun 19
Total with taxes and fees
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Walkable Townhouse with Garage & Yard, 45 min to NYC!

Walkable Townhouse with Garage & Yard, 45 min to NYC!
West Side
9.6 out of 10, Exceptional, (7 reviews)
"Place was clean, organized. A little odd to find but there was parking, the location felt safe. Would stay again."
United States
Dave J.
$701 nightly
The price is $766
Jun 21 - Jun 22
Total with taxes and fees
Walkable Townhouse with Garage & Yard, 45 min to NYC!

Stylish Home With Free ParkingFA

Stylish Home With Free ParkingFA
Downtown Stamford
$354 nightly
The price is $401
Jun 18 - Jun 19
Total with taxes and fees
Stylish Home With Free ParkingFA
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

Find out more about Chappaqua

Everything you need to know about Chappaqua vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chappaqua vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chappaqua vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chappaqua vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chappaqua. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chappaqua in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $135 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chappaqua rentals

At Expedia, we put the best Chappaqua vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chappaqua rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chappaqua vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chappaqua. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

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?

Cheerful Home in Yonkers NY: This vacation home rental near Chappaqua comes with WiFi so you can feel at home during your trip.

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 Jacob Burns Film Center Theater 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.