Pleasantville Vacation Rentals from ￥12,716: Search Short-Term Rentals

Q: What are some of the best vacation rentals in Pleasantville?

Family Home In the Heart of the Village of Chester : This vacation home rental near Pleasantville is located near the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the books in this rental home to help you unwind.

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Vacation Rentals in Pleasantville

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Recommended hotels in Pleasantville

"Great place to stay!"

Suite, Kitchenette, Ocean View (Split Level) | Private kitchenette | Mini-fridge, coffee/tea maker

"Loved everything. It's original quirkyness and excellent restaurant downstairs. So good we ate there both nights."

￥40,232 total

includes taxes & fees

Jul 11 - Jul 12

"The location and view were excellent. "

￥30,448 total

includes taxes & fees

Jul 11 - Jul 12

"Can’t beat the price for this location. Would definitely stay here again when we come back to Lunenburg."

￥18,343 total

includes taxes & fees

Jul 11 - Jul 12

Oceanfront Honeymoon King Room with Sunporch | Water view

"Great stay !"

￥33,864 total

includes taxes & fees

Jul 16 - Jul 17

Comfort Cabin, 2 Double Beds, Kitchen, Ocean View | 1 bedroom, premium bedding, memory foam beds, free WiFi

"Excellent place to stay"

￥25,459 total

includes taxes & fees

Jul 15 - Jul 16

"We had great service, helpful staff, very accommodating "

￥40,220 total

includes taxes & fees

Jul 14 - Jul 15

Comfort Room, Garden View | 1 bedroom, down comforters, in-room safe, free WiFi

"Great place with a very helpful staff and absolutely amazing breakfast. Will stay there again. "

￥21,926 total

includes taxes & fees

Jul 15 - Jul 16

Standard Room, 1 Queen Bed | 4 bedrooms, desk, free WiFi, bed sheets

"Owner was great explaining where to go to visit sites and local restaurants Great place to stay "

￥23,729 total

includes taxes & fees

Jul 19 - Jul 20

"Great place! The hosts are wonderful and we meet at many nice people from all over the world. I'll definitely stay here again."

￥22,011 total

includes taxes & fees

Jul 13 - Jul 14

"Margaret was a wonderful boast. This house has a lot of history and it is so very charming to be at. Breakfast was wonderful. "

￥19,260 total

includes taxes & fees

Jul 23 - Jul 24

"Lovely place to stay So close to walk to restaurants and shops"

￥36,422 total

includes taxes & fees

Jul 14 - Jul 15

"Beautiful quiet cabins with local trails to enjoy and explore. The sauna was fantastic and we loved the decor! So easy to access our room. Highly recommend!"

￥38,420 total

includes taxes & fees

Jul 14 - Jul 15

Cabin, Multiple Beds, Shared Bathroom | 1 bedroom, desk, free WiFi

"It was ok but I found it very expensive for only 1 plug in and no shower. I did like the location and staff were very friendly. "

￥14,496 total

includes taxes & fees

Jul 17 - Jul 18

"Location is great Friendly staff"

￥23,909 total

includes taxes & fees

Jul 17 - Jul 18

Suite, 1 King Bed, Non Smoking (One-Bedroom) | Desk, free cribs/infant beds, rollaway beds, free WiFi

"Nice place good room clean "

￥23,463 total

includes taxes & fees

Jul 20 - Jul 21

"Good spot. We would stay again. "

￥14,989 total

includes taxes & fees

Jul 11 - Jul 12

"We had a good time, restaurant is very nice - lots of veg options. "

￥28,941 total

includes taxes & fees

Aug 10 - Aug 11

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Find out more about Pleasantville

Search for holiday rentals in Pleasantville on Expedia! You can easily find your home rentals, villas, holiday apartments in Pleasantville using one of the methods below:

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Look no further and take a look at our great range of rental properties in Pleasantville!

Recent reviews of Pleasantville properties

5/5 Excellent

"Loved our room! It was clean and cozy with a great view of the ocean. Owners are lovely and friendly. A great spot for family’s and couples. Would happily stay here again and would recommend to others looking for a wonderful place to stay. "

A verified traveler stayed at Atlantic View Motel and Cottages

Posted 3 days ago

5/5 Excellent

"We had a fantastic stay at this historic B&B, set in a beautifully preserved 1800s home that still carries its old-world charm. Margaret, our host, was incredibly welcoming and truly showcased warm Canadian hospitality. She made us feel right at home from the moment we arrived. The atmosphere was cozy and peaceful, and we especially loved Chevy, the adorable house dog who added a special touch to our visit. Would absolutely stay here again—highly recommended for anyone looking for a unique and heartwarming experience!"

A verified traveler stayed at Miller House By the Bay

Posted 5 days ago

5/5 Excellent

Wonderful stay

"Magnolia Inn in Mahone Bay may have opened in 2024, but it’s housed in a beautifully restored historic property dating back to 1879. We were lucky to stay in the master bedroom on the second floor, which featured a spacious, modern bathroom. Each room includes a mini-fridge, smart TV, and Keurig coffee maker for added comfort. The first floor offers inviting shared spaces, including a cozy sitting room, a large dining area, and a quiet library—perfect if you need to get some work done. The entire inn is spotless and thoughtfully organized. Craig, the owner, was incredibly gracious and welcoming, and their summer staff (whose name we sadly forgot) was equally kind and helpful. We truly enjoyed our stay and would love to return."

A verified traveler stayed at Magnolia Inn

Posted 9 days ago

Frequently asked questions

Can I find vacation rentals in Pleasantville?

Yes, we give you a choice of vacation rentals close to top sights in Pleasantville, or you can choose a more secluded option if you'd like a relaxing place to stay.

What are some of the best vacation rentals in Pleasantville?

Family Home In the Heart of the Village of Chester: This vacation home rental near Pleasantville is located near the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the books in this rental home to help you unwind.

What’s there to see and do in Pleasantville?

While exploring the area, visit family-friendly sights like Fisheries Museum of the Atlantic, or get outside and enjoy nature at Woodland Gardens. In the larger area, you’ll find Bridgewater Mall and Wile Carding Mill Museum.

What’s a vacation rental in Pleasantville like?

A vacation rental is a private property where you can stay for a few weeks or just a few days in Pleasantville. Vacation rentals provide amenities such as kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about cleanliness, vacation rentals can offer a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great option for a family trip or a small group gathering.

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Pleasantville Vacation Rentals

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Vacation Rentals in Pleasantville

Recommended hotels in Pleasantville

Smugglers Cove Inn

Salt Shaker Deli & Inn

The Dockside Inn & Restaurant

Brigantine Inn & Suites

Rum Runner Inn

Atlantic View Motel and Cottages

Bluenose Lodge

Rose & Thistle Bed & Breakfast

The Homeport Motel

Fairmont House Bed & Breakfast

Miller House By the Bay

Magnolia Inn

Black Forest Cabins

Oakhill Pines Campground

Travelodge by Wyndham Bridgewater

Days Inn & Conference Center by Wyndham Bridgewater

Bridgewater Hotel

Best Western Plus Bridgewater Hotel & Convention Centre

Find out more about Pleasantville

Recent reviews of Pleasantville properties

Atlantic View Motel and Cottages

Smugglers Cove Inn

Travelodge by Wyndham Bridgewater

The Dockside Inn & Restaurant

Miller House By the Bay

Rum Runner Inn

The Homeport Motel

Fairmont House Bed & Breakfast

Magnolia Inn

Frequently asked questions