Holiday houses in Middleton

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Middleton

Guests agree: these stays are highly rated for location, cleanliness and more.

%{current} / %{total}1 / 1
Top Guest favourite
Cottage in Canning
4.96 out of 5 average rating, 135 reviews

A-Frame by the Bay

Slow down and soak up the beauty of the Bay of Fundy at this oceanfront A-frame in Scots Bay. Just steps from the shore and a 5-minute walk to the Cape Split trailhead, it’s perfect for hiking, paddling, and relaxing by the water. Sleeps up to 5 with cozy, coastal charm. Enjoy beach fires, dramatic tides, and local gems like Saltair Nordic Spa (25 mins), The Long Table Social Club, and award winning Valley wineries & breweries (20-40 mins). A peaceful place to reconnect with nature—and yourself.

Superhost
Home in Kingston
4.84 out of 5 average rating, 152 reviews

The Dog Pound

Visiting the Annapolis Valley? We have the perfect spot for you to rest after a day of exploring! We are centrally located with access to everything the valley has to offer. From the many local craft breweries, farms, wineries, gorgeous hiking trails, to CFB Greenwood’s Air Force Museum, there is SO much to experience! The Dog Pound is a 3 bedroom + den private home. Minimally designed to make you feel at ease at the end of your day. Onsite at Roofhound Brewing for a bonus dining experience!

Guest favourite
A cottage is situated among trees, offering a view of the Bay of Fundy in the distance. A wooden deck features seating arrangements, and a gravel pathway leads toward the water. The early morning light creates a serene atmosphere.
Home in Middleton
4.84 out of 5 average rating, 19 reviews

Ultra Private Oceanfront Cottage with Sunset Views

Renovated top to bottom in 2019, this stylish cottage is nestled in perfect privacy by the trees with spectacular views of the Bay of Fundy! Start the day with local sourced coffee and teas, in a well-appointed kitchen. Spend your time exploring the shore via private beach access, or watching seals at the nearby park at low tide. Spectacular sunsets are sure to impress, especially from the look-off on the ledge! After the sun goes down, enjoy a fire roasting marshmallows under the stars.

Guest favourite
A single-story gatehouse is framed by mature trees displaying vibrant autumn foliage. The exterior is white, complementing the warm colors of the leaves. A gravel pathway leads to the entrance, enhancing the inviting atmosphere of the property.
Home in Aylesford
4.97 out of 5 average rating, 207 reviews

The Gatehouse at Maple Brook

For business or pleasure, enjoy your stay in our spacious, bright one bedroom gatehouse. With all the conveniences of home, the central location allows you to explore the richness of the Annapolis Valley. The property is surrounded by mature trees and developing landscaping. Fully equipped for short or long stays with washer/dryer, dishwasher, queen bed, full living and dining areas. Kitchen has Keurig, microwave and full stove and fridge. On Highway 1 and close to exit for Highway 101.

Top Guest favourite
A serene lakeside view is captured with sunlight glistening on the water. The beach is lined with gentle waves, and a wooden dock is visible leading into the lake. A railing runs along the deck where seating is provided, set against lush greenery.
Cottage in Middleton
4.93 out of 5 average rating, 90 reviews

Serene lakefront living. Two bedroom cottage.

Relax with the whole family at this peaceful paradise on Trout Lake, New Albany, NS. Enjoy magical sunsets from the large lakeside patio, comfortably furnished screen room or firepit. Take in the scenery via kayaks, paddle boat or bicycles. A quick float or a short walk with water shoes will take you to a swimming area with a floating dock complete with cup holders & reclining seats. BBQ & full kitchen on site. WiFi, Sat TV, & outside/inside games provided for your entertainment.

Top Guest favourite
The exterior view of the holiday house is presented, showcasing a charming, shingled structure with a sloped roof. Lush greenery surrounds the building, including flowering bushes and manicured grass, under clear blue skies. A chimney can be seen on the side of the house.
Home in Annapolis Royal
4.96 out of 5 average rating, 149 reviews

Holiday House

Hello and welcome to the holiday house at Hummingbird Hill! Conveniently located between exits 21 and 22 off the 101 hwy, we are the ideal location for travelers looking to cross on the Digby ferry. This single level house has all the necessary amenities and is accessible to all. Our large property boasts gardens, fire pits, and yard games. The Rosette forestry trail is also open to all visitors of humming bird hill. We hope you will join us in our little piece of paradise.

Top Guest favourite
A charming cottage is perched on stilts amidst lush green foliage. Large windows provide expansive views, allowing natural light to fill the space. The surrounding landscape features a blend of trees and grass, creating a peaceful and serene atmosphere.
Cottage in Margaretsville
4.89 out of 5 average rating, 142 reviews

Margaretsville Cottage

Take it easy at this unique and tranquil getaway. Located on the North shore of The Bay of Fundy, this home will capture your heart with the most spectacular views on the Bay and the most breathtaking sunsets. The wall of windows will give you the ultimate view of the Bay. Sit on the outdoor deck and enjoy the breeze, smell the campfires on the beach or watch the tides come and go. Take a stroll along the beach, visit the HIstoric LIghthouse or pop into the Art Shack.

Guest favourite
The charming two-story home features a welcoming front porch and a gabled roof. Lush green trees surround the property, providing shade. A gravel pathway leads to the entrance, and a red vehicle is visible in the driveway. The landscape includes decorative plants and bushes.
Home in Middleton
4.95 out of 5 average rating, 59 reviews

Peaceful Central Valley home w/ CalmGardens&wifi

This peaceful home comes with amenities such as Wi-Fi and your first day free coffee/ and tea . The Keurig machine is a K Cup and Carafe maker. If you want to go to restaurants, shops, and cafes, we're within walking distance. Tim Hortons a short drive away. In the heart of the fabulous Annapolis Valley. It will enchant you with its unique charm. Shop the local fruit markets, antique shops, and craft stores. Golf nearby. A Short drive to the wineries and the Bay of Fundy.

Guest favourite
An aerial view showcases the cottage nestled among dense trees, with a clear path leading to a private waterfront. A firepit is visible by the lake's edge, surrounded by natural landscaping, offering a peaceful retreat in nature.
Cottage in Middleton
4.84 out of 5 average rating, 129 reviews

Waterfront Cottage on Lake with Hot Tub + Rec Room

Escape to the tranquility of nature with our spacious 2-bedroom cottage, perched on the edges of Waterloo Lake. Centrally located in the heart of Annapolis Valley; you are within driving distance to some of Nova Scotia's best destinations. With a 150-foot waterfront access you get to enjoy stunning sunrises and sunsets every day. The perfect retreat for families or groups of friends seeking a relaxing getaway, our cottage offers the ultimate in coziness and fun.

Top Guest favourite
Home in Lunenburg
5 out of 5 average rating, 163 reviews

Ocean Front #3 HotTub Sunset RoofTopDeck BBQ 2bath

Waterfront Cottage: Huge deck, sun sets, Private Hot Tub: 6 Person tub for 2. Panoramic Water Views: Modern Cabin: privacy and a peaceful environment. Large Deck: outdoor living space both you can take in the sun or retreat into the share. Nature Retreat with wildlife Romantic Escape: for couples, Heated floors, Shower tower, queen master, an extra guest could sleep on the couch. Super private chefs kitchen. Well equipped for all seasons.

Top Guest favourite
A modern log cottage is nestled among tall trees, softly illuminated by string lights. The structure features a welcoming porch with seating, enhancing a connection with nature. A clear path leads to the entrance, surrounded by a natural landscape of grass and stones.
Cottage in Greenfield
5 out of 5 average rating, 188 reviews

The Harmony Grand at Molega Lake

Harbour Acres Cottages offering: 5⭐"The Harmony Grand". A private modern log cottage perched on the serene shores of Molega Lake; Nova Scotia's South Coast cottage country. Experience this two bedroom, full bathroom, kitchen, & living room lakefront accommodation for either a short overnight stay or a longer vacation. We cater to all travelers! Breakfast is included*

Top Guest favourite
A modern villa is illuminated at night, featuring large glass windows that provide expansive views. The structure is set on a grassy slope, with outdoor seating and a grill visible on the patio, enhancing the outdoor living space.
Loft in Berwick
4.93 out of 5 average rating, 131 reviews

Bay of Fundy 1BR Loft

Panoramic views of the Fundy. (The cliffs of Fundy has been designated UNESCO Global Geopark site) Inside or out feel like your on the water. Everything has been designed to please the traveler. Easy access all year round, a romantic getaway, a writers retreat, storm watching enthusiasts or a friends long weekend.Harbour villa west will make you want to return for more.

Popular amenities for Middleton holiday rentals