Vacation rentals in Pleasantville

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Top-rated vacation rentals in Pleasantville

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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$27,727 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$30,176 GYD per night

Guest favorite

Home in White Plains

4.86 out of 5 average rating, 148 reviews

Bright&Comfy 2bed/1ba in quiet White Plains duplex

Bright, comfortable & quiet! Just outside downtown White Plains, this home has a relaxing living space with thoughtful touches. It offers easy accessibility to New York City (35 min Via Metro North) and Westchester (via highways and local buses). The house is set up for WFH, with great wifi via Verizon. It's an easy jump off spot for a fun weekend in Westchester. It comes with a dedicated parking spot, never worry about your vehicle! Bars, restaurants, shopping, groceries are all minutes away!

Aug 19 – 26

G$37,029 GYD per night

Guest favorite

Bungalow in Hastings-on-Hudson

4.92 out of 5 average rating, 718 reviews

★Tiny House Cottage 35 min to NYC on Hudson River★

The most popular Airbnb in the area! FREE private driveway too. A few blocks to the Hudson River. Super charming, slightly quirky, private Shangri-La w/backyard chickens in the artistic & quaint Rivertowns, 35 min. from NYC. The Tiny House escape is reminiscent of sleep away camp, though tastefully curated w/eclectic art & furnishings. Sleeping loft nest w/8 step ladder or pull out sofa bed. E-fireplace inside. Firepit outside. Stars galore. 2 patios, yard, hammock, gardens. Read on...

Jul 1 – 8

G$33,480 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$59,716 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$32,382 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$17,628 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$27,621 GYD per night

Guest favorite

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 14 – 21

G$31,383 GYD per night

Guest favorite

Guesthouse in Suffern

4.91 out of 5 average rating, 112 reviews

Private Studio w/Full Kitchen & Bath

Our place is a private, stand-alone building separate from our house, and is cleaned thoroughly between guests including disinfecting all hard surfaces. Private cottage with full kitchen and bath in Suffern, NY. Quick walk to train & bus to NYC. Right off I-87, I-287 (NY & NJ), & NJ Rt. 17. Close to shopping & local restaurants. Off-Street parking & outdoor picnic area. NO CLEANING FEE!

May 17 – 24

G$22,006 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$29,680 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$23,086 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Pleasantville vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Pleasantville's top sights

Wood & Fire7 locals recommend

Southern Table kitchen & Bar7 locals recommend

The Pleasantville Diner4 locals recommend

Jean-Jacques' Culinary Creations10 locals recommend

Jacob Burns Film Center33 locals recommend

Pub Street NY6 locals recommend

Other great vacation rentals in Pleasantville

Guest favorite

Guest suite in Hartsdale

4.88 out of 5 average rating, 114 reviews

Haven in Hartsdale! Private guest suite & bathroom

Jul 6 – 13

G$24,739 GYD per night

Superhost

Earthen home in Ossining

4.87 out of 5 average rating, 144 reviews

The Babbling Brook

Aug 22 – 29

G$26,775 GYD per night

Guest favorite

Guesthouse in Norwalk

4.99 out of 5 average rating, 208 reviews

Adorable one-bedroom guesthouse with parking

Jul 6 – 13

G$25,663 GYD per night

Guest favorite

Apartment in Peekskill

4.84 out of 5 average rating, 115 reviews

Little haven by the woods

Mar 28 – Apr 4

G$26,982 GYD per night

Guest favorite

Apartment in Harrison

4.96 out of 5 average rating, 247 reviews

Luxury Private Apartment - Walk to Train for NYC!

Mar 20 – 27

G$26,896 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$25,314 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$20,801 GYD per night

Guest favorite

Guest suite in Croton-on-Hudson

4.99 out of 5 average rating, 94 reviews

Enchanting Farmhouse Suite w/ pool and sauna

Sep 23 – 30

G$46,414 GYD per night

Show all

Quick stats about vacation rentals in Pleasantville

Total rentals
10 properties
Local attractions
Wood & Fire, Southern Table kitchen & Bar, and The Pleasantville Diner
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
660 reviews

Vacation rentals in Pleasantville

Top-rated vacation rentals in Pleasantville

Apartment in Mount Kisco

Cottage in Cortlandt

Home in White Plains

Bungalow in Hastings-on-Hudson

Apartment in Ossining

Barn in Mount Kisco

Guest suite in Haverstraw

Guesthouse in Mahopac

Guest suite in White Plains

Guesthouse in Suffern

Guesthouse in Peekskill

Apartment in Ardsley

Vacation rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Pleasantville vacation rentals

Stay near Pleasantville's top sights

Other great vacation rentals in Pleasantville

Guest suite in Hartsdale

Earthen home in Ossining

Guesthouse in Norwalk

Apartment in Peekskill

Apartment in Harrison

Apartment in Brookfield

Apartment in Pleasantville

Guest suite in Croton-on-Hudson

Quick stats about vacation rentals in Pleasantville

Total rentals

Local attractions

Popular amenities

Wifi availability

Family-friendly rentals

Total number of reviews

Destinations to explore