Vacation rentals in Town of Middleton

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Top-rated vacation rentals in Town of Middleton

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Superhost

An inviting guest suite features a spacious bed with a soft blue patterned comforter. A television is positioned opposite the bed, and a chair is placed nearby. Natural light filters in through light curtains, illuminating the warm wooden flooring.

Loft in Kentville

4.84 out of 5 average rating, 358 reviews

Winemakers Inn, Newly renovated guest suite.

We are offering a upstairs guest suite in our home in the beautiful Annapolis Valley. We live in a quiet neighborhood minutes from Kentville ,New Minas ,Wolville. We have a pool and deck with a BBQ in season that we will share. We are close to popular hiking / snowshoeing trails ,wineries and shopping. We are within walking distance of Valley Regional Hospital .We are not set up for long term living. Any questions message me. Enjoy your stay. Our cats name is peanut she is out side a lot

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, 107 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.

Guest favorite

A private hot tub with bubbling water is shown in the foreground. Behind it, the geodesic dome is visible, framed by trees and wooden decking. The clear sky reflects light on the dome's geometric structure, enhancing the serene ambiance.

Dome in Springfield

4.97 out of 5 average rating, 104 reviews

The Fishing Dome (2) - Lakefront - hot tub - Sauna

Escape to our adult-only lakefront dome, a fusion of nature and luxury. Experience unparalleled tranquility and refined elegance amidst serene surroundings. Unwind on the private patio with a mesmerizing fire table and soak in the private hot tub, surrounded by soothing nature sounds. Embark on aquatic adventures with kayaks and paddle boards. Gather around the fire pit for memorable evenings. Rejuvenate in the panoramic sauna with breathtaking lake vistas. Book now and create lifetime memories.

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, 127 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.

Guest favorite

The exterior of the cottage is framed by lush greenery, featuring a welcoming porch with a red door. Natural light bathes the facade, showcasing the wooden siding and scenic surroundings. Trees provide a sense of privacy and tranquility in the landscape.

Guesthouse in Granville Beach

4.95 out of 5 average rating, 128 reviews

Cozy, Spacious Cottage on Peaceful Property

This cozy cottage nestled in quiet Granville Beach is close enough to all amenities of Annapolis Royal, but tucked away into a serene property surrounded by greenery with a view of the river. This cottage comes with everything you need and more, a fully functional kitchen with stove/ oven, mini fridge, microwave and sink. A bathroom with toilet and shower and a comfy living space, just outside of the bedroom separated by a sliding door. This is the perfect place to have a house away from home.

Top guest favorite

A cozy living space is presented with a spacious bed and a comfortable seating area. A small dining table is set for two, adorned with decorative plates. Natural light fills the area through a window, illuminating the modern kitchenette and accent decor.

Guest suite in North Alton

4.99 out of 5 average rating, 200 reviews

The Loft

Welcome to The Loft! This is a private second floor unit.This unit is available year around.We are located on a beautiful golf course with beautiful views. The short term rentals are a independant business and a separate business from the golf course. We offer private independant living with your own private entrance.We do not have a stove in the kitchenette but have lots of kitchen gadgets to make almost any meal. Close to Kentville,Coldbrook and New Minas. Minutes off of the 101 exit 13.

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.

Top guest favorite

An aerial view showcases a serene cottage nestled among lush greenery, with trees lining the path leading to the property. The bay stretches in the background, offering a stunning view of the water and distant shores.

Cottage in Centreville

4.97 out of 5 average rating, 194 reviews

Eagle's Bluff - Seaside Cottage in Halls Harbour

"Eagle's Bluff" is a cozy & charming cottage tucked away above the rocky shores of the Bay of Fundy a stone's throw from beautiful Halls Harbour--home of the world's highest tides! You can completely disconnect and enjoy a relaxing getaway on this private property with walking trails throughout or enjoy Netflix on the available Wifi. We offer a perfect home base for your Annapolis Valley adventures--wineries, Wolfville, Cape Split, Grand Pre, Blomidon--and we'd be thrilled to host you!

Top 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, 216 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 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, 138 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.