Chappaqua Vacation Rentals from $135: Search Short-Term Rentals

Q: 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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chappaqua vacation rentals

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

Historic District

Rebecca H.

$758 nightly

Jul 13 - Jul 14

Total with taxes and fees

Standard Room, 1 King Bed, Main Building | Property entrance

Guesthouse at Norwalk Inn

Historic District

Ronbert

$348 nightly

Jul 5 - Jul 6

Total with taxes and fees

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

Historic District

Ricky W.

$341 nightly

Jul 1 - Jul 2

Total with taxes and fees

Spacious Retreat with Game Room and Fire Pit

West Norwalk

$692 nightly

Jun 24 - Jun 25

Total with taxes and fees

Waterview House Walking Distance from Cove Beach

Cove - East Side - Shippan

Scott H.

$893 nightly

Jun 19 - Jun 20

Total with taxes and fees

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Cove - East Side - Shippan

james w.

$624 nightly

Jun 28 - Jun 29

Total with taxes and fees

Stamford Hideaway w/ Fire Pit

Cove - East Side - Shippan

$322 nightly

Jul 8 - Jul 9

Total with taxes and fees

New Beach Home near Stamford Downtown/Shippan

Cove - East Side - Shippan

Steve G.

View all properties

Find vacation rentals that suit your style

Aparthotels

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Chappaqua Hotel Reviews

LIV Hotel Bronx - Newly Built

10/10 Excellent

"My husband and I stay here overnight. I have to say the customer service was excellent. The cleanliness of the room was perfect. The set up of the room was perfect. The ambience when you walk into the hotel is a good vibe the bed was so comfortable and the shower was awesome we had a great day the only thing missing was that there was no iron to iron your clothes and Parking was extremely hard other than that. I think we had an excellent day."

Tarrytown House Estate

10/10 Excellent

"Property was beautiful everywhere we looked. Pool was clean and staff was attentive. Nice and well behaved crowd, except in the end a few loud kids that were playing rough (I believe it was an exception). Nice views, clean and comfy room, easy check in/out. Minor complaints: giant chess game needs maintenance, one of the umbrellas in the pool was broken and it took a while until someone took it away (it felt and it could hurt someone). Id love more food options in the front desk (ran out of ice cream and other stuff). Gym and sauna also great, we played a lot of pickeball. Fun!!"

Hotel Nyack, a JdV by Hyatt Hotel

8/10 Good

"Overall experience and accommodations were positive. We plan to return to the area within the next 3-6 months and plan stay at this property again, due to it’s convenient location. We hope to see improvements in the areas described below. We enjoyed breakfast in the hotel’s restaurant. The cost was a bit steep (for breakfast), but we anticipated that and so we weren’t surprised. The food was good, the presentation was appealing and the serving size plentiful. Our waitress was welcoming and attentive. I requested my eggs scrambled “soft” - they missed the mark on the “soft” part, but it was not a big deal. Next time we visit we will skip the coffee; we found it to be bitter. We’ll get our coffee from Nyack Bagels or Dunkin; their coffee is consistently good. The front office team was welcoming and helpful - good first impression. We requested bottle water, and the front desk gave it to us with a smile. We requested housekeeping each day. Surfaces were not wiped down, e.g. the bedside tables, which are glass/reflective. The toilet room door was missing a handle, which made it difficult to exit the toilet. The shower did not drain properly. The iron/ironing board was not re-stored, but was left on the table/desk. The iron was placed on its side and water ran out all over the table/desk. There are no cups in the room, which you need in order to put water in the iron. Except for the first day, our room did not have the right number of towels/wash cloths. We had to ask for them"

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.

Chappaqua Vacation Rentals

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Chappaqua vacation rentals

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

Guesthouse at Norwalk Inn

King Bedroom Studio - Victorian Guest House Studio - Luxury Apartment

Spacious Retreat with Game Room and Fire Pit

Waterview House Walking Distance from Cove Beach

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Stamford Hideaway w/ Fire Pit

New Beach Home near Stamford Downtown/Shippan

Stylish Home With Free ParkingZA

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

Stylish Home and Cozy

Stylish Home with Free Parking

Stamford Suites

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

Modern Luxe 1BR Apt in Downtown Stamford

The Gallery in Downtown Stamford

Solara – Luxury 1BR Downtown

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

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

Stylish Home With Free ParkingFA

Find vacation rentals that suit your style

Top Chappaqua Hotel Reviews

LIV Hotel Bronx - Newly Built

Find out more about Chappaqua

Explore a world of travel with Expedia

Frequently asked questions

Expedia's Latest Trends

Go further with the Expedia app