Vacation rentals in Chappaqua

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Top-rated vacation rentals in Chappaqua

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Guest favourite

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.

Dec. 30 – Jan. 6

$193 CAD per night

Guest favourite

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.

Jun. 6 – 13

$338 CAD per night

Guest favourite

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

Jun. 5 – 12

$362 CAD 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.

Jan. 12 – 19

$203 CAD per night

Guest favourite

Apartment in Ossining

4.94 out of 5 average rating, 297 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

$411 CAD per night

Guest favourite

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

Oct. 22 – 29

$232 CAD per night

Guest favourite

Earth homes 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 4 – 11

$181 CAD per night

Guest favourite

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. 17 – 24

$119 CAD per night

Guest favourite

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

Nov. 14 – 21

$184 CAD per night

Superhost

Guest suite in White Plains

4.87 out of 5 average rating, 164 reviews

1BR close to White Plains train station

From NYC by train 40 minutes, and walking from my apartment to the train only 7 minutes, but coming back is uphill so takes longer. Convenient for shopping, and dining, and walking distance to downtown White plains. Please read the entire description, and make sure the place, you are looking for, before you reserve. Our apartments are completely renovated and have separate entrances. Please ask me a monthly rate.

Oct. 7 – 14

$210 CAD per night

Guest favourite

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

$198 CAD per night

Guest favourite

Home in Dobbs Ferry

4.92 out of 5 average rating, 306 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

$90 CAD 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 favourite

Cottage in Bedford

4.98 out of 5 average rating, 121 reviews

Tudor Cottage In Heart of Bedford

Jan. 22 – 29

$614 CAD per night

Superhost

Apartment in Ardsley

4.9 out of 5 average rating, 379 reviews

Lovely and well-appointed suite with full privacy

Mar. 13 – 20

$159 CAD per night

Superhost

Home in Ossining

4.84 out of 5 average rating, 125 reviews

Lower Hudson Valley Idyllic Retreat

Feb. 22 – Mar. 1

$608 CAD per night

Superhost

Guest suite in Piermont

4.85 out of 5 average rating, 381 reviews

Cozy private apartment with Hudson River views

May 4 – 9

$165 CAD per night

Guest favourite

Apartment in Croton-on-Hudson

4.98 out of 5 average rating, 267 reviews

Luxury 2bd⭐Comfort+Style⭐

Feb. 23 – Mar. 2

$314 CAD per night

Guest favourite

Guesthouse in Bedford Hills

4.91 out of 5 average rating, 112 reviews

Barrett's Sanctuary

Jan. 5 – 12

$432 CAD per night

Guest favourite

Home in Stamford

4.98 out of 5 average rating, 131 reviews

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING

Aug. 30 – Sep. 6

$161 CAD per night

Guest favourite

Apartment in Pleasantville

4.79 out of 5 average rating, 48 reviews

Beautiful Studio Apartment in Perfect Location

Nov. 24 – Dec. 1

$141 CAD 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

Vacation rentals in Chappaqua

Top-rated vacation rentals in Chappaqua

Apartment in Mount Kisco

Cottage in Pound Ridge

Apartment in Ossining

Apartment in Peekskill

Apartment in Ossining

Barn in Mount Kisco

Earth homes in Ossining

Guest suite in Haverstraw

Guesthouse in Mahopac

Guest suite in White Plains

Guesthouse in Peekskill

Home in Dobbs Ferry

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 Bedford

Apartment in Ardsley

Home in Ossining

Guest suite in Piermont

Apartment in Croton-on-Hudson

Guesthouse in Bedford Hills

Home in Stamford

Apartment in Pleasantville

Quick stats about vacation rentals in Chappaqua

Total rentals

Local attractions

Popular amenities

Wifi availability

Family-friendly rentals

Total number of reviews

Destinations to explore