Pleasantville Vacation Packages
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Your Pleasantville Vacation
With every last detail organized before you take off, our Pleasantville vacation packages mean you can focus more on having a good time. Whether you base yourself in the neighborhood of Garden Lots, which is great for watersports, or someplace else, this lively city offers a wealth of discoveries. Any trip to Pleasantville needs a well-designed itinerary. Fill yours with big-name attractions like Halifax and Southwestern Railway Museum, Osprey Ridge Golf Course and Fort Point Museum. A few clicks is all it takes to craft your dream Pleasantville vacation on Expedia.
Top Pleasantville Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Mamas by the sea B&B
Price was CA $721, price is now CA $550 per person
CA $550
per person
Jun 29 - Jul 4
found 3 hours ago
Roundtrip flight included
Toronto (YYZ) to Halifax (YHZ)
10/10 Exceptional! (120 reviews)
Kim was lovely, and the location right on the water was perfect. Her little dog Zoey is very friendly. Would definitely stay again.
Reviewed on Oct 17, 2025
Sandman Signature Dartmouth Hotel & Suites
Price was CA $1,841, price is now CA $1,225 per person
CA $1,225
per person
Jun 20 - Jun 26
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Halifax (YHZ)
9.4/10 Exceptional! (2,428 reviews)
Room was great, loved that it had a kitchenette. Pool was good but a little crowded. Overall was a great stay.
Reviewed on Apr 27, 2026
The Sutton Place Hotel Halifax
Downtown Halifax
Price was CA $1,451, price is now CA $1,062 per person
CA $1,062
per person
May 28 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Hamilton (YHM) to Halifax (YHZ)
9.6/10 Exceptional! (2,112 reviews)
water pressure horrible ! Lighting was poor ! Bar is good
Reviewed on Apr 27, 2026
South West Mermaid Inn
Price was CA $924, price is now CA $709 per person
CA $709
per person
Jun 29 - Jul 4
found 8 hours ago
Roundtrip flight included
Toronto (YYZ) to Halifax (YHZ)
8.2/10 Very Good! (759 reviews)
Pool not operational for winter I guess. Older place but pretty good location and value...lots of parking
Reviewed on Apr 6, 2026
Chateau Bedford, Trademark Collection by Wyndham
Birch Cove
Price was CA $1,559, price is now CA $1,198 per person
CA $1,198
per person
Jun 20 - Jun 26
found 1 day ago
Roundtrip flight included
Hamilton (YHM) to Halifax (YHZ)
9.2/10 Wonderful! (2,113 reviews)
The bed height was too high for an accessible room. A person in wheelchair cannot independently get into the bed if it is higher than the average bum height. Please slightly lower the bed height.
Reviewed on Apr 25, 2026
Pleasantville Hotel Deals
Floating Cottage on The LaHave River close to beaches, golf, on Lighthouse Route
Pleasantville NS
10/10 Exceptional! (89 reviews)
Everything was above and beyond our expectations, the property is amazing and every single detail was perfect, sharp knives, 100% cotton bedding and towels, the absolute best tasting tap water amazing,surprises to discover on short outings! Picture perfect views and the best stars at night.We hated ...
Reviewed on Aug 22, 2025
Smugglers Cove Inn
139 Montague Street Lunenburg NS
Fully refundableReserve now, pay when you stay
The price is CA $183 per night from May 9 to May 10
CA $183
CA $209 total
May 9 - May 10
includes taxes & fees
9/10 Wonderful! (788 reviews)
A very pleasant stay.
Reviewed on Apr 27, 2026
The Homeport Motel
167 Victoria Road Lunenburg NS
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Apr 29 to Apr 30
CA $145
CA $165 total
Apr 29 - Apr 30
includes taxes & fees
9/10 Wonderful! (578 reviews)
Great, clean
Reviewed on Apr 27, 2026
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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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
