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Check prices for these dates

Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
In one month
Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Compare 7 B&B in Pleasantville with updated reviews, rates, and availability.

Stanton House Inn
Reception

Stanton House Inn

3.5 star property
9.6 out of 10, Exceptional, (144)
"Extremely friendly and helpful staff. Clean, quiet and charming !"
Stanton House Inn
West Lane Inn
Terrace/patio

West Lane Inn

3.5 star property
9.8 out of 10, Exceptional, (49)
"Wonderful inn with great breakfast, very safe, wonderful new bathrooms, comfortable clean beds with excellebt dining options nearby."
$374 nightly
The price is $430
Jul 2 - Jul 3
Total includes taxes and fees
West Lane Inn
Honey Maple Grove BnB
42-inch TV with digital channels, heated floors

Honey Maple Grove BnB

4.0 star property
9.6 out of 10, Exceptional, (4)
"Charming and quiet…. perfect bed and breakfast!"
Honey Maple Grove BnB
Charming Grand View/Lake Loft in Brewster with WiFi, AC
Interior

Charming Grand View/Lake Loft in Brewster with WiFi, AC

10.0 out of 10, Exceptional, (3)
"Had a fantastic stay! Property is so beautiful and relaxing. Orestes does everything possible to make guests feel at home...cooks a breakfast with home grown veggies and herbs... delicious!"
Charming Grand View/Lake Loft in Brewster with WiFi, AC
The Kittle House Inn
Property entrance

The Kittle House Inn

3.5 star property
8.2 out of 10, Very Good, (411)
"Beautiful place to stay with a great staff "
The Kittle House Inn
Cozy Homeva Chatterton WP
Porch

Cozy Homeva Chatterton WP

3.0 star property
Cozy Homeva Chatterton WP
Cozy Homeva Battle Hill WP
Penthouse Suite At Cozy Homeva | 1 bedroom, desk, laptop workspace, blackout drapes

Cozy Homeva Battle Hill WP

3.0 star property
Cozy Homeva Battle Hill WP
Cozy Homeva Kensico WP
Front of property

Cozy Homeva Kensico WP

3.0 star property
10.0 out of 10, Exceptional, (1)
"Eva & her son Matthew were very friendly & accommodating."
Cozy Homeva Kensico WP
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

What is the nightly rate for a Bed and Breakfast in Pleasantville?
Prices for B&Bs in Pleasantville often vary, but you can find a great deal from $430 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Pleasantville B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Pleasantville?
The best time to book a B&B in Pleasantville is during the vibrant spring months of April to June. This period not only showcases Pleasantville's blooming gardens and lush landscapes but also welcomes a host of outdoor events and festivals that celebrate the area's rich culture. As the weather warms, temperatures typically range from the mid-50s to the low 80s Fahrenheit, creating ideal conditions for leisurely strolls and outdoor dining.

April, in particular, stands out as an excellent time to visit, with mild temperatures and fewer crowds compared to the peak summer months. Visitors can immerse themselves in the local art scene, attend farmers' markets, and enjoy the picturesque parks that come alive during this season. The pleasant climate lends itself to outdoor activities like hiking and picnicking in the nearby nature reserves, making it a great getaway for those seeking relaxation and connection with nature.

For travelers looking for budget-friendly options, consider planning your trip in November, when Pleasantville experiences a quieter atmosphere. This month offers beautiful autumn foliage and a chance to enjoy the local shops and cozy cafes without the hustle and bustle of peak season.
What is the difference between a Pleasantville B&B and a hotel?
Every Pleasantville B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Pleasantville B&Bs.