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, 148 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 20 – 27

$116 per night

Guest favorite

Cottage in Pound Ridge

4.93 out of 5 average rating, 170 reviews

Adirondacks in Westchester

Located on quiet, private 5.5 acre estate with swimmable lake, fantastic landscape. Complete privacy, like being in the Adirondacks, but just one hour from NYC. Cottage has high end appliances (Sub-Zero, Miele) with separate road and entrance. Perfect for a getaway from NYC and easily accessible by car or train (Stamford station). Can be combined with Adirondacks in Westchester 2 to provide an additional bedroom in a separate building to accommodate a total of four guests. Excellent wifi.

Feb 17 – 24

$203 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

Sep 27 – Oct 4

$201 per night

Superhost

Apartment in Peekskill

4.84 out of 5 average rating, 115 reviews

Little haven by the woods

This is a walk-out basement with two private entrances, and it’s own private outside area. The patio has comfy furniture with a bbq. The kitchen is small, yet efficient with large windows. The bedroom is cozy and comfy with a large smart tv on the wall. The bedroom has a 3/4 wall dividing it from the rest of the apt, but no actual door. So it could be considered a “studio”. We are steps from the trail heads into Blue Mt park. We’re also walking distance to the metro north & downtown.

Mar 22 – 29

$112 per night

Guest favorite

Apartment in Ossining

4.94 out of 5 average rating, 298 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 15 – 22

$250 per night

Guest favorite

Barn in Mount Kisco

4.91 out of 5 average rating, 538 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

Feb 21 – 28

$135 per night

Guest favorite

Earthen home in Ossining

4.87 out of 5 average rating, 143 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

May 8 – 15

$113 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:)

Oct 17 – 24

$74 per night

Guest favorite

Guesthouse in Mahopac

4.96 out of 5 average rating, 107 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

Sep 6 – 13

$109 per night

Guest favorite

Guesthouse in Peekskill

4.94 out of 5 average rating, 206 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

Oct 28 – Nov 4

$114 per night

Guest favorite

Home in Dobbs Ferry

4.93 out of 5 average rating, 307 reviews

Small cozy room in historic 1828 Dobbs Ferry home.

This is a sweet warm room with twin bed chest of drawers, desk and hanging closet with shelves. I have a 2nd larger room with two twin beds in it, listed separately, and also a very small bedroom with a slightly narrower bed with a curtain across the doorway. Please note: I have one cat. So if you are allergic, maybe not a good choice for you.

Jan 10 – 17

$55 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!

Jan 23 – 30

$368 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

Superhost

Home in Ossining

4.84 out of 5 average rating, 125 reviews

Lower Hudson Valley Idyllic Retreat

Oct 6 – 13

$359 per night

Superhost

Guest suite in White Plains

4.87 out of 5 average rating, 164 reviews

1BR close to White Plains train station

Oct 7 – 14

$120 per night

Superhost

Apartment in Ardsley

4.9 out of 5 average rating, 379 reviews

Lovely and well-appointed suite with full privacy

Feb 12 – 19

$93 per night

Superhost

Guest suite in Piermont

4.85 out of 5 average rating, 381 reviews

Cozy private apartment with Hudson River views

$92 per night

Guest favorite

Guesthouse in Bedford Hills

4.91 out of 5 average rating, 112 reviews

Barrett's Sanctuary

Oct 19 – 26

$282 per night

Superhost

Home in Yorktown Heights

4.88 out of 5 average rating, 118 reviews

Cozy winter getaway 1 hr from NYC!

Oct 5 – 12

$292 per night

Guest favorite

Apartment in Pleasantville

4.79 out of 5 average rating, 48 reviews

Beautiful Studio Apartment in Perfect Location

Mar 21 – 28

$87 per night

Guest favorite

Guesthouse in North Castle

4.98 out of 5 average rating, 41 reviews

Magical 1700's 1 bedroom cottage

Dec 14 – 21

$180 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 wifi, over 10 homes with free parking, over 10 homes with air conditioning, over 10 homes with a kitchen, 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

Home in Ossining

Guest suite in White Plains

Apartment in Ardsley

Guest suite in Piermont

Guesthouse in Bedford Hills

Home in Yorktown Heights

Apartment in Pleasantville

Guesthouse in North Castle

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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