Holiday rentals in Pleasantville

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Top-rated holiday rentals in Pleasantville

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Guest favourite

Flat 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.

20–27 Aug

£115 per night

Guest favourite

Home in White Plains

4.86 out of 5 average rating, 147 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!

25 Aug – 1 Sept

£162 per night

Superhost

Flat 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.

22–29 Mar

£121 per night

Guest favourite

Bungalow in Hastings-on-Hudson

4.91 out of 5 average rating, 716 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...

8–15 Nov

£139 per night

Superhost

Guest suite in Piermont

4.85 out of 5 average rating, 381 reviews

Cozy private apartment with Hudson River views

This cozy apartment just one block from the Hudson River, is on the ground level of a house, with a separate entrance offering complete privacy. This modern space has a fully equipped kitchen, beautiful bathroom, comfy queen bed, reading chair, books galore, and a desk. Located in the adorable town of Piermont, it has the feel of a country retreat, a waterfront town, and it's an easy commute to Manhattan. As of Nov. 2022, the WIFI has been upgraded and it is now RELIABLE & HIGH-SPEED.

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

21–28 Feb

£138 per night

Guest favourite

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

8–15 May

£108 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:)

17–24 Oct

£71 per night

Guest favourite

Guest house 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

6–13 Sept

£110 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.

7–14 Oct

£125 per night

Guest favourite

Guest house 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

28 Oct – 4 Nov

£118 per night

Guest favourite

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.

10–17 Jan

£53 per night

Holiday rentals for every style

Get the amount of space that is right for you

Popular amenities for Pleasantville holiday 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 holiday rentals in Pleasantville

Guest favourite

Flat in Ossining

4.94 out of 5 average rating, 298 reviews

Hudson River Peaceful Getaway

15–22 Sept

£244 per night

Guest favourite

Home in Stamford

4.98 out of 5 average rating, 131 reviews

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING

30 Aug – 6 Sept

£96 per night

Superhost

Flat in Piermont

4.81 out of 5 average rating, 234 reviews

Piermont Cozy Haven

11–18 Jul

£101 per night

Guest favourite

Flat in Pleasantville

4.79 out of 5 average rating, 48 reviews

Beautiful Studio Apartment in Perfect Location

21–28 Mar

£84 per night

Guest favourite

Guest suite in Croton-on-Hudson

4.99 out of 5 average rating, 94 reviews

Enchanting Farmhouse Suite w/ pool and sauna

17–24 Nov

£200 per night

Guest favourite

Home in White Plains

4.98 out of 5 average rating, 40 reviews

Cozy renovated 3bed White Plains Home

23–30 Aug

£317 per night

Guest favourite

Guest suite in Sleepy Hollow

4.98 out of 5 average rating, 44 reviews

Sleepy Hollow Private Apartment Airbnb

19–26 Aug

£101 per night

Guest favourite

Flat in Harrison

4.89 out of 5 average rating, 46 reviews

Quiet and Cozy

28 Sept – 5 Oct

£78 per night

Show all

Quick stats about holiday 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

Holiday rentals in Pleasantville

Top-rated holiday rentals in Pleasantville

Flat in Mount Kisco

Home in White Plains

Flat in Peekskill

Bungalow in Hastings-on-Hudson

Guest suite in Piermont

Barn in Mount Kisco

Earthen home in Ossining

Guest suite in Haverstraw

Guest house in Mahopac

Guest suite in White Plains

Guest house in Peekskill

Home in Dobbs Ferry

Holiday rentals for every style

Hotels

Unique stays

Homes

Popular amenities for Pleasantville holiday rentals

Stay near Pleasantville's top sights

Other great holiday rentals in Pleasantville

Flat in Ossining

Home in Stamford

Flat in Piermont

Flat in Pleasantville

Guest suite in Croton-on-Hudson

Home in White Plains

Guest suite in Sleepy Hollow

Flat in Harrison

Quick stats about holiday rentals in Pleasantville

Total rentals

Local attractions

Popular amenities

Wifi availability

Family-friendly rentals

Total number of reviews

Destinations to explore