Vacation rentals in Chappaqua

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Top-rated vacation rentals in Chappaqua

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Guest favorite

Apartment in Mount Kisco

4.93 out of 5 average rating, 149 reviews

Cozy 1 Bdrm Apt; Privt Entry; 5 min walk to train

This cozy apartment is on the lower level of a house, just a 5 minute walk to town and the Harlem Line, Metro North Train stop. A separate entrance to the apt offers complete privacy. This gorgeous space has a fully equipped kitchen, bathroom, comfy twin beds . Located in the adorable town of Mount Kisco, allowing you to take strolls to access restaurants, boutique shops, library, park and bars. It has the feel of a country retreat, a quaint town, and it's an easy commute to White Plains or NYC.

Aug 24 – 31

G$27,718 GYD per night

Guest favorite

Cottage in Cortlandt

4.99 out of 5 average rating, 159 reviews

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

Aug 3 – 10

G$30,165 GYD per night

Superhost

Home in Ossining

4.84 out of 5 average rating, 125 reviews

Lower Hudson Valley Idyllic Retreat

Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.

May 6 – 13

G$69,159 GYD per night

Guest favorite

Apartment in Ossining

4.95 out of 5 average rating, 100 reviews

Gorgeous 1 BR w/High End Finishes, Heated BA Floor

Unwind at this peaceful retreat a short walk from downtown Ossining and Hudson River front parks. Designed with end to end comfort, beautifully decorated, and featuring a gorgeous open kitchen and entertaining room, in this space you can relax and step away from it all. Highlights include: 2nd floor walk-up High End Appliances and all Finishes Heated bathroom floors Contactless entry Off-street parking 1/2 block from multiple parks Weekly discount available Come stay here! You’ll love it

Nov 22 – 29

G$54,032 GYD per night

Guest favorite

Apartment in Ossining

4.94 out of 5 average rating, 302 reviews

Hudson River Peaceful Getaway

Self check-in and private entrance. Parking for two cars. Peaceful apartment on the Hudson River. Train to NYC (Scarborough Station) is an 8 minute walk through historic neighborhood. Arcadian Mall (Grocery store, Starbucks, etc) 5 minute walk. Rivers views from inside and from three patios (1 on entrance side, 2 on River side). We only allow declawed cats because they can scratch and damage our expensive furniture and carpets. Most house trained dogs are welcome :)

Sep 14 – 21

G$59,695 GYD per night

Guest favorite

Barn in Mount Kisco

4.91 out of 5 average rating, 539 reviews

NY Rustic Cottage Getaway

minimum of 3 nights during Covid-19 in order to keep things safe for guests... Prices are slightly elevated winter due to the cost of oil Just 50 min North of NYC (Metro North 5 min away) great for artists, writers, yogi's and creative types or people just wanting to get away from the hustle and bustle, city amenities near by. (Photo Shoots, Seminars, Workshops welcome-Call For different Rates) Tag & Follow Nina’s Cottage on Insta! @ninas_airbnb

Mar 17 – 24

G$32,371 GYD per night

Superhost

Earthen home in Ossining

4.87 out of 5 average rating, 144 reviews

The Babbling Brook

Unique 2 room and 3rd room ( full bath) with backyard and babbling brook with 5 minute ride to train into NYC and 45 minute car ride to midtown Manhattan (with no traffic, lol) Totally renovated with gorgeous large bedroom overlooking backyard and brook. Private entrance with patio. Private driveway with parking spot. For 1 night only guests add $15.00 cleaning fee. Here is a 2 minute Video of "THE BABBLING BROOK" https://www.youtube.com/watch?v=CRUac3qSOm0

Aug 22 – 29

G$26,766 GYD per night

Guest favorite

Guest suite in Haverstraw

4.95 out of 5 average rating, 293 reviews

Haverstraw Hospitality Suite

Quiet & cozy suite, with a comfortable full bed & private bathroom in newly renovated garden (basement) level of a single-family home. WiFi/air conditioning & heat unit/FiOS cable - roku TV. Coffee/tea available. Rollaway available for an extra bed. The neighborhood is quiet, and parking is available in the driveway. Feel free to come and go as you please -- we hope our guests feel like this is their home away from home:)

Jan 12 – 19

G$17,621 GYD per night

Guest favorite

Guesthouse in Mahopac

4.96 out of 5 average rating, 110 reviews

Sunny Lakeview Guesthouse

Art and light filled spacious studio with panoramic views overlooking lake Mahopac. Walkable to swimming/paddleboarding; skating/ice fishing. Many fine restaurants or casual takeout options, and boasting an excellent coffee shop. Train ride from Grand Central to Croton Falls, then a 12 minute drive or shuttle ride. Close to Fahenstock Park, Cold Springs, Beacon, Ridgefield,or walk up the hill to the trails of Volz park

Jan 4 – 11

G$27,611 GYD per night

Guest favorite

Guesthouse in Peekskill

4.94 out of 5 average rating, 207 reviews

Peekskill Carriage House Downtown Studio

Located close to the center of town, this is the perfect launchpad to experience local restaurants, coffee houses, the Paramount Theater, shopping, etc. and a short drive to stunning hikes, the Hudson Valley and beyond. The apartment is ideal for one or two and features a kitchenette, bathroom, dining island, comfortable queen bed, and couch. peekskillcarriagehouse.com

Jul 10 – 17

G$29,669 GYD per night

Guest favorite

Cottage in Bedford

4.98 out of 5 average rating, 121 reviews

Tudor Cottage In Heart of Bedford

Come stay in open fresh air!!!! Discount for lengthy stays!!! Delightful Tudor Cottage set in heart of Bedford, next to BRLA and numerous barns, preserves and great towns for shopping and dining. Recently renovated with two bedrooms, bathroom, full kitchen and washer dryer. The perfect country get away only 45 mins away from NYC!

Sep 23 – 30

G$83,832 GYD per night

Guest favorite

Apartment in Ardsley

4.9 out of 5 average rating, 380 reviews

Lovely and well-appointed suite with full privacy

Charming suite with a private entrance, bathroom, indoor parking and dining area with kitchen amenities. Conveniently located in Westchester, and is accessible by the I-87, Henry Hudson, Sprain and Saw Mill Parkways; only a thirty minute drive to NYC. Near a deli, grocery, bakery, Carvel, CVS and a selection of restaurants.

Jan 13 – 20

G$23,078 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Chappaqua vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Chappaqua's top sights

Crabtree's Kittle House Restaurant & Inn6 locals recommend

Gedney Park6 locals recommend

DeCicco & Sons4 locals recommend

Lexington Square Cafe5 locals recommend

Hacienda la Paloma4 locals recommend

Craft Pizza & Beer4 locals recommend

Other great vacation rentals in Chappaqua

Guest favorite

Cottage in Cortlandt

5.0 out of 5 average rating, 104 reviews

Cottage at Peekskill Hollow

Jan 6 – 13

G$51,450 GYD per night

Guest favorite

Cottage in Valhalla

4.96 out of 5 average rating, 223 reviews

Charming private 1BR apt. Easy access to NYC

Jul 14 – 21

G$66,165 GYD per night

Guest favorite

Guesthouse in Bedford

4.92 out of 5 average rating, 173 reviews

Private Guest Studio

Aug 23 – 30

G$45,282 GYD per night

Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 184 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Sep 4 – 11

G$25,305 GYD per night

Guest favorite

Guesthouse in Bedford Hills

4.91 out of 5 average rating, 112 reviews

Barrett's Sanctuary

Jan 14 – 21

G$58,784 GYD per night

Guest favorite

Apartment in Pleasantville

4.79 out of 5 average rating, 48 reviews

Beautiful Studio Apartment in Perfect Location

Feb 2 – 9

G$20,794 GYD per night

Guest favorite

Guesthouse in North Castle

4.98 out of 5 average rating, 42 reviews

Magical 1700's 1 bedroom cottage

Feb 9 – 16

G$42,993 GYD per night

Guest favorite

Apartment in Mount Kisco

4.9 out of 5 average rating, 62 reviews

Comfy, Clean & Convenient 1 Bed Village Apartment

Dec 13 – 20

G$33,507 GYD per night

Show all

Quick stats about vacation rentals in Chappaqua

Total rentals
10 properties
Local attractions
Crabtree's Kittle House Restaurant & Inn, Gedney Park, and DeCicco & Sons
Popular amenities
Kitchen, Wifi, and Pool
Wifi availability
10 properties include access to wifi
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
480 reviews

Frequently Asked Questions

What are the most popular amenities for House Rentals in Chappaqua?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with free parking, over 10 homes with a kitchen, over 10 homes with air conditioning, over 10 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there family-friendly vacation rentals in Chappaqua?
Chappaqua has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Chappaqua have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Chappaqua. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Chappaqua?
Experience the best of Chappaqua with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Chappaqua have a kitchen?
Absolutely! We offer over 10 house rentals with a kitchen in Chappaqua. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chappaqua have wifi?
Absolutely! We offer over 10 house rentals with wifi in Chappaqua. Enjoy a tailored experience with all the comforts you desire.

Vacation rentals in Chappaqua

Top-rated vacation rentals in Chappaqua

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Chappaqua vacation rentals

Stay near Chappaqua's top sights

Other great vacation rentals in Chappaqua

Cottage in Cortlandt

Cottage in Valhalla

Guesthouse in Bedford

Apartment in Brookfield

Guesthouse in Bedford Hills

Apartment in Pleasantville

Guesthouse in North Castle

Apartment in Mount Kisco

Quick stats about vacation rentals in Chappaqua

Total rentals

Local attractions

Popular amenities

Wifi availability

Family-friendly rentals

Total number of reviews

Frequently Asked Questions

What are the most popular amenities for House Rentals in Chappaqua?

Are there family-friendly vacation rentals in Chappaqua?

Do house rentals in Chappaqua have air conditioning?

How much does it cost to stay in house rentals in Chappaqua?

Do house rentals in Chappaqua have a kitchen?

Do house rentals in Chappaqua have wifi?

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