Park City Resort Rentals - 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 w/Deck From US $1,361
         

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10.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Security/Safety
Luxury NY Home with Free Parking From US $381
         

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8.0 (1 Review)
House
  • Parking
  • Security/Safety
  • Business Services
Cozy 1BR/2 Queen Beds/Free Parking/Private Stay From US $814
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern 1BR Apt/Free Parking/Near NYC From US $782
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Lovely house in Tarrytown From US $437
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Stylish Tarrytown Studio - Walk to Train & Main St From US $345
         

Hudson River Views: Briarcliff Manor Home w/Deck From US $1,307
         

9.8 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Pleasantville

Over 149+ 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 $2,157
         

Luxury NYC Retreat with Free Parking From US $1,604
         

8.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Comfortable & Spacious 3BR /Free Parking/Great for Families From US $1,429
         

4.8 (3 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly

Top-Rated Vacation Rentals with a Pool in Pleasantville

Over 42+ Top-Rated Vacation Rentals with a Pool in or Near Pleasantville
Baymont by Wyndham White Plains - Elmsford From US $164
         

8.4 (1688 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Sheraton Tarrytown Hotel From US $164
         

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8.4 (1003 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 $159
         

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7.9 (1332 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Tarrytown House Estate From US $140
         

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7.8 (842 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Sleepy Hollow Hotel, a Dolce by Wyndham From US $111
         

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7.4 (8 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Pleasantville

Over 55+ Pet-Friendly Vacation Rentals in or Near Pleasantville
NYC-Area Escape Near River, Trails & MTA! From US $659
         

8.2 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
NYC-Area Escape Near River, Trails and MTA! From US $689
         

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8.7 (3 Reviews)
House
  • Parking
  • Pet Friendly
  • View
3BR Prime Luxury NY - Free Parking From US $1,263
         

6.0 (1 Review)
Apartment
  • Parking
  • Pet Friendly
  • Security/Safety

Large Vacation Homes & Villas in Pleasantville

Over 28+ Large Vacation Homes & Villas in or Near Pleasantville
3 Mi to Downtown: Spacious White Plains Home From US $655
         

9.2 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • Balcony/Terrace
3 Mi to Downtown: Spacious White Plains Home From US $768
         

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8.0 (4 Reviews)
House
  • Parking
  • View
  • Security/Safety
Luxury NYC Home Game Room Free Parking From US $778
         

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4.0 (1 Review)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Ultimate 3BR Getaway 4 Queen Beds Sleeps 16 Parking From US $1,172
         

Wheelchair Accessible Vacation Homes in Pleasantville

Over 35+ Wheelchair Accessible Vacation Homes in or Near Pleasantville
Courtyard by Marriott Tarrytown Westchester County From US $328
         

Courtyard by Marriott Tarrytown Westchester County From US $184
         

Pleasantville Vacation Rentals and Airbnb Places to Stay Under $200

Over 22+ Pleasantville Vacation Rentals and Airbnb Places to Stay Under $200
Cozy tiny log cabin on 14 acres From US $199
         

9.6 (5 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
American Room At Cozy Homeva From US $104
         

Amazing Large Private Studio!+ From US $170
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Great for pets! Quaint apartment w Backyard, walk to Main Street, Music Hall From US $160
         

Instantly Bookable Vacation Homes in Pleasantville

Over 43+ Instantly Bookable Vacation Homes in or Near Pleasantville
Polished 1BR w/Accessible Room Features + Sauna From US $391
         

Luxury Urban Retreat + Spacious & Stylish From US $535
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
NEW! Cozy Pleasantville Retreat Unit 2 From US $363
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Near NYC! | Stylish Guestroom From US $361
         

About Pleasantville Vacation Rentals

With more than 158 Pleasantville vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Parkcityresortrentals 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 Parkcityresortrentals 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 833.36 ft² on average, with prices averaging US $632 a night.

Parkcityresortrentals 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 67
Hotels 49
Holiday Apartments 31
Cottages 4
Villas 3
B&B 1
Cabin Rentals 1
Others 1

Use these Quick Filters to Find a Vacation Rental in Pleasantville

Pro Tip: Parkcityresortrentals makes it easy to compare the best listings on Parkcityresortrentals homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Parkcityresortrentals 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

Pleasantville Vacation Rental Frequently Asked Questions

How many vacation rentals are available in Pleasantville?

Currently, the total number of properties listed in 2026 is over 158 in the Pleasantville area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Pleasantville.