Holiday rentals in Town of Middleton

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.

The Fishing Dome - 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.

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!

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.

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.

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.

Cozy Victorian Tiny Home in Tree Oasis

Only 6 mins from historical Annapolis Royal. Last minute bookings always welcome. 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.

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.

The Owl's Nest Wilderness Cottage

Come experience farm life for yourself and stay at The Owl’s Nest Wilderness Cottage – our private, off grid retreat that boasts open pastures, wildlife and a warm Nova Scotia welcome! Tucked between Bear River, Annapolis Royal, and Kejimkujik National Park, Owl King Orchard is a 70 acre farm dotted with highland cattle, sheep, goats and winding forest trails. If you’re coming to unwind or to explore the local area, there is plenty of fun to be had all year ‘round.