Holiday houses in Town of Middleton

Cozy Victorian Tiny Home in Tree Oasis

Only 6 mins from historical Annapolis Royal. Last minute bookings always welcome. Off-season prices in effect. 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.

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!

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.

Ocean Front #4 Hot Tub 2bdrm huge deck BBQ 2bath

- Oceanfront, Pier, Boat Launch, - Massive Deck: Ideal for lounging entertaining, dining, High-Top Table, BBQ, Firewall: Ensures safety and peace of mind. - Hot Tub: Unwind and enjoy the serene ocean views. - Kitchen: induction cooktop and wall oven, ideal for preparing gourmet meals. - Two Bedrooms, Two Baths: The home includes a spacious master bedroom with a king-size bed and an en suite bath. - Second Bathroom: tub for a relaxing soak. HOOKd 4 perfect retreat best of oceanfront living.

Unique Lighthouse Cottage with Incredible Views

Nestled on the hill above the Bay of Fundy, the lighthouse-shaped cottage boasts a cozy retreat with one bedroom, capturing the essence of coastal living. The highlight is the top-floor living room, where panoramic windows frame the beautiful seascape. From this elevated vantage point, guests can unwind in the warmth of the living room while enjoying the view of the sea caves, creating a tranquil and picturesque haven suspended between land and sea. Just a quick walk down the hill to the beach.

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.

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.

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.

Seaside Escape - Wake to Waves & Panoramic Views

Relax and recharge at The Shore, our cozy coastal retreat nestled along the dramatic Bay of Fundy shoreline. Just 40 minutes from the picturesque vineyards of Wolfville and 90 minutes from Halifax. Wake up to the sound of waves, stroll along the beach where the world's highest tides shape the rugged coast, and marvel at breath taking sunsets from your spacious private deck. At night, unwind under a canopy of stars in one of the most peaceful settings you’ll ever experience.

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.

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.

Whispering Oaks Studio

** studio is strictly for non smokers/non vapers** Welcome to our cozy modern studio nestled in the heart of the Annapolis Valley, the perfect location to set up camp and explore all the Valley has to offer. Greenwood, the home of 14 Wing and the Military Aviation Museum a short drive away, 10 mins to Margaretsville, 45 mins the the quaint town of Wolfville. 60 mins to Digby with its scallops and whale watching. 90mins to Halifax.