Outdoor Places - Vacation Rentals in Pleasantville

Neighbor's house - Welcome! From US $198
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Hudson River Views Briarcliff Manor Home with Deck From US $1,143
         

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10.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Accessibility
The Kittle House Inn From US $253
         

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8.2 (412 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • TV
Lovely house in Tarrytown From US $446
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Stylish Tarrytown Studio - Walk to Train & Main St From US $275
         

Hudson River Views: Briarcliff Manor Home w/Deck From US $942
         

9.8 (12 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
3 Mi to Downtown: Spacious White Plains Home From US $419
         

9.0 (10 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace

Luxury Places to Stay in Pleasantville

Over 126+ Luxury Places to Stay in or Near Pleasantville
2BDRM COTTAGE IN PLEASANTVILLE From US $3,564
         

New
Cottage
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating
Spectacular Mansion with pool/spa - close to NYC From US $1,907
         

Top-Rated Vacation Rentals with a Pool in Pleasantville

Over 36+ Top-Rated Vacation Rentals with a Pool in or Near Pleasantville
Sheraton Tarrytown Hotel From US $164
         

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8.4 (1002 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Baymont by Wyndham White Plains - Elmsford From US $134
         

8.2 (1483 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Sheraton Tarrytown Hotel From US $159
         

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8.0 (263 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Baymont by Wyndham White Plains - Elmsford From US $98
         

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7.9 (1358 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Tarrytown House Estate From US $140
         

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7.6 (909 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Pleasantville

Over 41+ Pet-Friendly Vacation Rentals in or Near Pleasantville
Luxury NYC Home Game Room Free Parking From US $778
         

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New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Elegant Hideaway Free Parking From US $293
         

6.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury NY Home with Game Room & Free Parking From US $712
         

5.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury NYC Retreat with Free Parking
New
From US $773
         

New
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Prime Luxury NYC: Free Parking + Mins away from Downtown
New
From US $720
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

Large Vacation Homes & Villas in Pleasantville

Over 22+ Large Vacation Homes & Villas in or Near Pleasantville
3 Mi to Downtown Spacious White Plains Home From US $768
         

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7.3 (3 Reviews)
House
  • Parking
  • View
  • Accessibility
Upscale 3BR Luxury NY Home - Prime Location + Free Parking
New
From US $355
         

Cozy family home From US $1,000
         

9.8 (13 Reviews)
House
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
Castle Retreat w/Pool, BBQ, Game Room & Pets OK! From US $1,378
         

9.0 (6 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Peaceful Mansion in White Plains. Close to everything From US $559
         

6.0 (3 Reviews)
Villa
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens

Wheelchair Accessible Vacation Homes in Pleasantville

Over 28+ Wheelchair Accessible Vacation Homes in or Near Pleasantville
Courtyard by Marriott Tarrytown Westchester County From US $183
         

Courtyard by Marriott Tarrytown Westchester County From US $164
         

Pleasantville Varoom and Airbnb Places to Stay Under $200

Over 23+ Pleasantville Varoom and Airbnb Places to Stay Under $200
Cozy Homeva Kensico WP From US $104
         

New
House
  • Air Conditioner
  • Parking
  • TV
Cozy tiny log cabin on 14 acres From US $199
         

9.6 (5 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Lovely one bedroom apartment in Westchester, NY! From US $126
         

Amazing Large Private Studio!+ From US $170
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Instantly Bookable Vacation Homes in Pleasantville

Over 26+ Instantly Bookable Vacation Homes in or Near Pleasantville
Luxury Urban Retreat + Spacious & Stylish
New
From US $431
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Elegant 1-bedroom Hideaway Free Parking
New
From US $330
         

New
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Near NYC! | Stylish Guestroom From US $342
         

New
Apartment
  • Air Conditioner
  • Parking
  • TV

About Pleasantville Vacation Rentals

With more than 135 Pleasantville vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Outdoorplaces and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Pleasantville.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Outdoorplaces Pleasantville, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Pleasantville. Places to stay near Pleasantville are 822.37 ft² on average, with prices averaging $544 a night.

Outdoorplaces makes it easy and safe to find and compare vacation rentals in Pleasantville with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Pleasantville

Type Count
Vacation Homes 54
Hotels with Suites 47
Holiday Apartments 24
Cottages 3
Villas 3
B&B 1
Cabin Rentals 1
Others 1

Use these Quick Filters to Find a Vacation Rental in Pleasantville

Pro Tip: Outdoorplaces makes it easy to compare the best listings on Outdoorplaces homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Outdoorplaces homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Pleasantville.

Weather in Pleasantville

View the weather forecast for Pleasantville before booking your Pleasantville Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F