Vacation rentals in Town of Middleton

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Town of Middleton

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

0 of 0 items showing

1 of 3 pages

Guest favorite

The rustic kitchen features a wood cookstove surrounded by stone walls, complementing locally sourced timber cabinetry. A dining table with chairs sits next to large windows, allowing natural light to illuminate the space. Open shelves display various kitchen essentials, enhancing functionality.

Cabin in Hampton

4.93 out of 5 average rating, 103 reviews

Ironwood Cottage

At the top of the North Mountain, this off grid tiny home features locally milled timber and stone construction, wood cookstove and panoramic sunset views over the Bay of Fundy. Soak in the tranquil sights and sounds from this cozy mountain perch. Located in a dark-sky preserve, star gazing is second to none. 140 acres of private forest, brookside sauna, and Snow Lake are yours to explore. Local hiking trails, waterfalls, lakes, Valleyview Provincial Park, Hampton Beach and lighthouse nearby.

Superhost

The living area features a gray sofa and an armchair, complemented by a wooden coffee table. A floor lamp provides soft lighting beside a window. The space is designed with a light color palette and has a fan mounted on the ceiling.

Home in Kingston

4.87 out of 5 average rating, 126 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!

Top guest favorite

A well-appointed bedroom features a spacious bed with striped bedding and accent pillows in rich colors. Soft bedside lamps provide warm lighting, while natural light enters through two windows framed by light curtains. A small nightstand complements the inviting atmosphere.

Guesthouse in Aylesford

4.97 out of 5 average rating, 152 reviews

Mid Valley Suite

This is a 2 bedroom 1.5 bath guesthouse, centrally located in the beautiful Annapolis Valley. Greenwood Air Force Base is 15 minutes away. Wolfville and its vineyards are 30 minutes away. At the other end of the Valley is Annapolis Royal, the first European settlement in North America. Peggy's Cove, Lunenburg, Digby, and Yarmouth are an easy drive. Please note: we are semi-rural, with a restaurant and convenience store close by. Groceries and a liquor store are in Berwick, 10 km to the east.

Top guest favorite

A blue single-story house is set within a lush green lawn, surrounded by trees. A picnic table is positioned nearby on the grass, offering a space for outdoor gatherings. The home features a white door and a window, framed by landscaping that enhances the natural setting.

Guest suite in Middleton

4.99 out of 5 average rating, 71 reviews

Elegant home away from home - Valley View

Away from it all and under the stars. This modern unit offers a relaxing, quiet experience. Conveniently located just off Hwy 101, close to amenities and the famous Bay of Fundy (highest tides in the world). Enjoy your own semi-private space in our backyard with a stunning view of the valley. See the sunrise while sipping your coffee, splash in the pool on hot days and have your BBQ at the picnic table. Look at the stars while the firepit keeps you cozy or snuggle up inside on those rainy days.

Top guest favorite

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

4.98 out of 5 average rating, 194 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.

Guest favorite

The exterior of the tiny house is illuminated by warm light emanating from the glass doors, highlighting its inviting entrance. The surrounding natural environment is visible in the dusk, with hints of trees and greenery blending into the evening sky.

Tiny home in Annapolis Royal

4.81 out of 5 average rating, 213 reviews

Cozy Victorian Tiny Home in Tree Oasis

Only 6 mins from historical Annapolis Royal. After October 12 2025 please contact first. Fast WIFI. Once used for horse carriages, I converted this into a fully self-contained tiny house/guest suite. (It has a kitchenette; however it is not suitable for large scale, full course cooking.) Spectacular views of North mountain, nestled in the famed fertile Annapolis Valley. Peach tree growing region. Railway turned nature trail practically across the street, perfect for cycling into town.

Guest favorite

A brown cottage with a red metal roof is positioned on a grassy lot overlooking the ocean. A staircase leads to a porch, and a picnic table is visible in the foreground, offering a spot for outdoor relaxation.

Cottage in Aylesford

4.88 out of 5 average rating, 104 reviews

Bay of Fundy cottage

Seated high on the North Mountain above the Bay of Fundy, this cottage offers open concept living/dining area with high ceiling, ocean views, and a beautiful porch for relaxing on a spacious lot with a fire pit for enjoying the outdoors. We are located in the beautiful Annapolis Valley only a short drive from the Town of Berwick. **Please note if bringing pets, that must be disclosed and approved before your arrival. There will be a pet cleaning fee for having pets on the property.

Top guest favorite

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

4.95 out of 5 average rating, 131 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.

Guest favorite

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

4.88 out of 5 average rating, 136 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.

Superhost

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

4.83 out of 5 average rating, 106 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 favorite

A hot tub is situated on a wooden deck, with steam rising gently from the water. The background features a serene view of rolling hills under a colorful sunset, creating a peaceful setting for relaxation.

Home in Kentville

4.98 out of 5 average rating, 338 reviews

Hot Tub 2 Bed House NEW Kentville A/C Valley Views

Welcome to “The Twelve" a luxury 2 bedroom home with sensational views privately set in the Annapolis Valley. Located just 15 minutes from Wolfville, it’s a perfect spot to explore the many wineries and craft breweries nestled across the valley. Be greeted by the bright and open layout, modern kitchen and sweeping views. Enjoy your favourite wine in your hot tub and embrace the breathtaking sunrises and sunsets from the private deck.

Guest favorite

A cozy deck features two black Adirondack chairs facing a small wooden table, providing a perfect spot to enjoy the sunset by the lake. The recently redone red Boler trailer is nestled among trees, with glimpses of the water visible just beyond.

Tiny home in New Albany

4.9 out of 5 average rating, 129 reviews

Lakefront Boler Trailer

Sleeps 2 only! This 13 foot 1974 Boler has been completely redone. Parked lakeside on the beautiful Zwickers Lake, just steps from the beach, the Boler is outfitted in with a dock and outdoor kitchen (BBQ, camp stove and propane). Bedding is not provided. A communal flush toilet bathroom is just 100 feet away. Firewood is available for purchase for $8 a bin. Come enjoy the spectacular sunsets!