Luxury Sicily Villa - Vacation Rentals in Pleasantville

The Black Crow Lodge with w/Hot Tub & Views From US $459
         

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10.0 (1 Review)
Villa
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace

Luxury Places to Stay in Pleasantville

Over 95+ Luxury Places to Stay in or Near Pleasantville
Zen Oceanfront Chalet- Hot Tub & Sauna - Private From US $770
         

10.0 (4 Reviews)
House
  • Air Conditioner
  • TV
  • Balcony/Terrace
Whitecaps Retreat Beach House From US $612
         

10.0 (133 Reviews)
House
  • Parking
  • Pet Friendly
  • TV
Whitecaps Summit Beach House From US $582
         

10.0 (104 Reviews)
House
  • Parking
  • Pet Friendly
  • TV
Luxury Coastal Dome - Private Hot Tub, Oceanfront Deck, Firepit & Parking From US $477
         

Coastal Dome Escape - Oceanfront, Private Hot Tub, Firepit and Deck From US $430
         

10.0 (21 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Balcony/Terrace

Top-Rated Vacation Rentals with a Pool in Pleasantville

Over 2+ Top-Rated Vacation Rentals with a Pool in or Near Pleasantville
Oakhill Pines Campground From US $87
         

7.3 (56 Reviews)
Other
  • Parking
  • Pool
  • Security/Safety
Oakhill Pines Campground From US $93
         

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9.0 (16 Reviews)
Cabin
  • Parking
  • Pool
  • Designated Smoking Area

Pet-Friendly Vacation Rentals in Pleasantville

Over 37+ Pet-Friendly Vacation Rentals in or Near Pleasantville
Whitecaps Cabana for Couples From US $247
         

10.0 (70 Reviews)
House
  • Parking
  • Pet Friendly
  • TV
King Bed Apt in Bridgewater near River and Trails From US $97
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Travelodge by Wyndham Bridgewater From US $152
         

8.2 (940 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Modern Cottage near Lunenburg - Ocean Views, Pet Friendly, Expansive Deck From US $370
         

2-bedroom apartment in charming Bridgewater with WiFi, AC. Enjoy your stay From US $175
         

10.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety
Large Backyard Oasis near River and Trails From US $155
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
Abigael’s Apt Suite 1 BR 2 BED in Central Bridgewater From US $159
         

9.0 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • Pet Friendly
ABBY’S APT Suite , 1 Queen Bed , 65” Curved TV, From US $122
         

8.4 (6 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Security/Safety

Large Vacation Homes & Villas in Pleasantville

Over 1+ Large Vacation Homes & Villas in or Near Pleasantville

Wheelchair Accessible Vacation Homes in Pleasantville

Over 2+ Wheelchair Accessible Vacation Homes in or Near Pleasantville
Travelodge by Wyndham Bridgewater From US $135
         

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7.8 (371 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pet Friendly
Days Inn by Wyndham Bridgewater Conference Center From US $130
         

7.4 (421 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Designated Smoking Area

Pleasantville Vacation Rentals and Airbnb Places to Stay Under $200

Over 36+ Pleasantville Vacation Rentals and Airbnb Places to Stay Under $200
Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater From US $182
         

Easter Sale 1BR Big Kitchen by River and Trails From US $73
         

9.5 (2 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • View
Days Inn & Conference Center by Wyndham Bridgewater From US $152
         

Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6. From US $179
         

8.8 (3 Reviews)
Apartment
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
King Bed Apt in Bridgewater near River and Trails From US $158
         

Instantly Bookable Vacation Homes in Pleasantville

Over 37+ Instantly Bookable Vacation Homes in or Near Pleasantville
A Quiet Riverside Cottage with 2 Fireplaces From US $213
         

10.0 (86 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • View
Shackup Cabin— Wood Fired Hot Tub & Near the beach From US $218
         

10.0 (5 Reviews)
Cabin
  • Parking
  • Balcony/Terrace
  • Security/Safety
Red Roof Bed & Breakfast From US $229
         

9.6 (9 Reviews)
Apartment
  • Air Conditioner
  • Parking
  • TV
Romantic Oceanfront Retreat - Hot tub From US $268
         

9.2 (12 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Luxury Oceanfront Home in Lunenburg From US $377
         

8.0 (2 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • TV
LaHaven Skippers Retreat From US $386
         

New
House
  • Parking
  • Designated Smoking Area
  • TV

About Pleasantville Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Luxurysicilyvilla 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 150.69 ft² on average, with prices averaging US $459 a night.

Luxurysicilyvilla 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
Villas 1

Use these Quick Filters to Find a Vacation Rental in Pleasantville

Pro Tip: Luxurysicilyvilla makes it easy to compare the best listings on Luxurysicilyvilla homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Luxurysicilyvilla 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 23°F       Low 2°F
March - May
High 65°F       Low 12°F
June - August
High 76°F       Low 49°F
September - November
High 65°F       Low 8°F

Pleasantville Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Pleasantville?

There are a lot of options in Pleasantville. If you plan on staying in the Pleasantville area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Pleasantville:

How many vacation rentals are available in Pleasantville?

Currently, the total number of properties listed in 2026 is over 1 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.