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, 150 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 4 – 11

G$42,654 GYD per night

Guest favorite

Home in White Plains

4.87 out of 5 average rating, 151 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!

Sep 18 – 25

G$37,023 GYD per night

Guest favorite

Bungalow in Hastings-on-Hudson

4.91 out of 5 average rating, 722 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...

Dec 25 – Jan 1

G$33,475 GYD per night

Guest favorite

Apartment in Ossining

4.94 out of 5 average rating, 308 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 27 – Oct 4

G$59,707 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

Jul 28 – Aug 4

G$32,378 GYD per night

Guest favorite

Guest suite in Haverstraw

4.95 out of 5 average rating, 298 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:)

Dec 14 – 21

G$17,625 GYD per night

Guest favorite

Apartment in Croton-on-Hudson

4.97 out of 5 average rating, 270 reviews

Luxury 2bd⭐Comfort+Style⭐

45 min train to Grand Central. Apt is 1.9mi to train, supermarket. Free PARKING. Two 4K TVs, 4K Blu-ray library, NFLX/AMZN/HBO/Apple TV. XBOX 1X. Fast WIFI. SS APPL, stocked kitchen. Bd1: adjustable queen, 50" 4K TV. Bd2: adj queen. Office area (desk, fast wifi), private porch. Sidewalks. 7 min walk to cafes, a bar, and restaurants. Car rental is 16 min walk. Hiking, kayaking. I LIVE NEARBY IN ANOTHER APT | $75 PET FEE |

Sep 29 – Oct 6

G$43,330 GYD per night

Guest favorite

Guesthouse in Mahopac

4.96 out of 5 average rating, 113 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

Oct 30 – Nov 6

G$27,443 GYD per night

Guest favorite

Guest suite in White Plains

4.87 out of 5 average rating, 166 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 25 – Nov 1

G$30,964 GYD per night

Guest favorite

Guesthouse in Peekskill

4.94 out of 5 average rating, 212 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

Sep 6 – 13

G$27,533 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!

Jul 24 – 31

G$80,177 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.

Mar 23 – 30

G$23,054 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

Sep 5 – 12

G$21,796 GYD per night

Superhost

Earthen home in Ossining

4.87 out of 5 average rating, 144 reviews

The Babbling Brook

Oct 21 – 28

G$26,771 GYD per night

Superhost

Apartment in Peekskill

4.84 out of 5 average rating, 116 reviews

Little haven by the woods

Jan 26 – Feb 2

G$26,029 GYD per night

Guest favorite

Cottage in Cortlandt

4.99 out of 5 average rating, 160 reviews

The Little Cottage in the Woods

Oct 24 – 31

G$28,060 GYD per night

Guest favorite

Guest suite in Tarrytown

4.94 out of 5 average rating, 211 reviews

Brand new private Studio in the heart of Tarrytown

Aug 13 – 20

G$53,730 GYD per night

Guest favorite

Apartment in Pleasantville

4.79 out of 5 average rating, 48 reviews

Beautiful Studio Apartment in Perfect Location

Feb 23 – Mar 2

G$21,218 GYD per night

Guest favorite

Guest suite in Sleepy Hollow

4.98 out of 5 average rating, 44 reviews

Sleepy Hollow Private Apartment Airbnb

Aug 19 – 26

G$25,058 GYD per night

Guest favorite

Guest suite in Croton-on-Hudson

4.99 out of 5 average rating, 95 reviews

Enchanting Farmhouse Suite w/ pool and sauna

Nov 18 – 25

G$47,234 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

Home in White Plains

Bungalow in Hastings-on-Hudson

Apartment in Ossining

Barn in Mount Kisco

Guest suite in Haverstraw

Apartment in Croton-on-Hudson

Guesthouse in Mahopac

Guest suite in White Plains

Guesthouse in Peekskill

Cottage in Bedford

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

Apartment in Peekskill

Cottage in Cortlandt

Guest suite in Tarrytown

Apartment in Pleasantville

Guest suite in Sleepy Hollow

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