Rsvp Cottages - Vacation Rentals in Pleasantville

Modern charming country cottage for long term availability From US $224
         

10.0 (3 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Ossining Vacation Rental Near River, Trails & Mta! From US $861
         

2BDRM COTTAGE IN PLEASANTVILLE From US $3,564
         

New
Cottage
  • Air Conditioner
  • Security/Safety
  • Fireplace/Heating
3 Mi to Downtown: Spacious White Plains Home From US $814
         

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New
Cottage
  • Air Conditioner
  • Parking
  • Balcony/Terrace

Luxury Places to Stay in Pleasantville

Over 149+ Luxury Places to Stay in or Near Pleasantville
Spectacular Mansion with pool/spa - close to NYC From US $2,107
         

Hudson River Views Briarcliff Manor Home with Deck From US $1,361
         

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10.0 (2 Reviews)
House
  • Parking
  • Pet Friendly
  • Accessibility
Hudson River Views: Briarcliff Manor Home w/Deck From US $1,307
         

9.8 (14 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
3BR Prime Luxury NY - Free Parking From US $1,263
         

6.0 (1 Review)
Apartment
  • Parking
  • Pet Friendly
  • Security/Safety
Cozy family home From US $1,182
         

9.8 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • TV

Top-Rated Vacation Rentals with a Pool in Pleasantville

Over 44+ Top-Rated Vacation Rentals with a Pool in or Near Pleasantville
Castle Retreat w/Pool, BBQ, Game Room & Pets OK! From US $898
         

9.2 (7 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Sheraton Tarrytown Hotel From US $164
         

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8.4 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Baymont by Wyndham White Plains - Elmsford From US $155
         

8.2 (1676 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 (1358 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool
Tarrytown House Estate From US $140
         

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7.8 (849 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly

Pet-Friendly Vacation Rentals in Pleasantville

Over 50+ Pet-Friendly Vacation Rentals in or Near Pleasantville
Lovely house in Tarrytown From US $436
         

10.0 (1 Review)
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
Luxury 3BR Home Game Room Free Parking From US $548
         

New
Apartment
  • Parking
  • Pet Friendly
  • Child Friendly
Modern 1BR Apt/Free Parking/Near NYC From US $312
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
NYC-Area Escape Near River, Trails & MTA! From US $716
         

8.2 (15 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury NYC Retreat with Free Parking From US $502
         

8.0 (1 Review)
House
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

Large Vacation Homes & Villas in Pleasantville

Over 27+ Large Vacation Homes & Villas in or Near Pleasantville
3 Mi to Downtown: Spacious White Plains Home From US $758
         

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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7.3 (3 Reviews)
House
  • Parking
  • View
  • Accessibility
Luxury NYC Home Game Room Free Parking From US $526
         

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New
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly

Wheelchair Accessible Vacation Homes in Pleasantville

Over 36+ 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 $192
         

Pleasantville Vacation Rentals and Airbnb Places to Stay Under $200

Over 25+ Pleasantville Vacation Rentals and Airbnb Places to Stay Under $200
Neighbor's house - Welcome! From US $198
         

10.0 (5 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
American Room At Cozy Homeva From US $104
         

Cozy tiny log cabin on 14 acres From US $199
         

9.6 (5 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Amazing Large Private Studio!+ From US $170
         

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

Instantly Bookable Vacation Homes in Pleasantville

Over 43+ Instantly Bookable Vacation Homes in or Near Pleasantville
Stylish Tarrytown Studio - Walk to Train & Main St From US $401
         

Luxury Urban Retreat + Spacious & Stylish From US $522
         

New
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
NEW! Cozy Pleasantville Retreat Unit 2 From US $369
         

New
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Cozy 1BR/2 Queen Beds/Free Parking/Private Stay From US $300
         

Polished 1BR w/Accessible Room Features + Sauna From US $401
         

About Pleasantville Vacation Rentals

With more than 4 Pleasantville vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rsvpcottages 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 Rsvpcottages 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 with prices averaging US $1,366 a night.

Rsvpcottages 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
Cottages 4

Use these Quick Filters to Find a Vacation Rental in Pleasantville

Pro Tip: Rsvpcottages makes it easy to compare the best listings on Rsvpcottages homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Rsvpcottages 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 4 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.