Holiday rentals in 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.

The Loft

Welcome to The Loft! Winter rate discount Jan -March. This is a private second floor unit. The Loft is available year around. We are located on a beautiful golf course with beautiful views. We offer private independant living with your own private entrance. Unit does not have a stove it does have lots of kitchen gadgets to make almost any meal. There are no added cleaning fees. Close to hospital,Kentville,Coldbrook and New Minas. Minutes off of the 101 exit 13.Clean, modern and safe units.

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.

Tall Pine Cove Cottage

Tall Pine Cove is a cottage property situated on beautiful Grand Lake. Built in 2019, the cottage features a private beach and is perfect for swimming, fishing and exploring, and relaxing. Located on a private road, you’ll be sure to find peace and quiet here. We offer a kayak and canoe to help you experience all that Grand Lake has to offer. End your days relaxing by the fire pit or sipping your favourite drink on the front deck overlooking the lake and taking in the dark sky preserve.

Cozy Cottage on South Shore. 30 min from Halifax!

A very cozy and peaceful place to base any vacation on the South Shore out of. Very close to hiking and ATV trails. No visible neighbors from the yard, lots of wildlife. Large parking areas. Interior is a mixture of new and re purposed materials. Appliances are small but functional, all the comforts of home but smaller. Double bed is incredibly comfortable. It is my home that I vacate for guests, and contains some sentimental decorations and items. RYA-2023-24-03271525339628999-1197

East Coast charm, cabin and hot tub by the river

The perfect location to explore the very popular South Shore of Nova Scotia. Close to beaches, cafes, restaurants, charming fishing villages and many other amenities. Come for a magical getaway. Tucked away in the woods along side a babbling brook. Enjoy morning coffee on the deck, BBQ your dinner overlooking the river, groove to our vintage record collection, keep toasty by the wood stove and float in the hot tub under the stars. This is a wonderful cabin experience you won't forget!

Historic East Coast Apartment *Private Sauna*

On your next valley get away, stay in charming Hantsport. This endearing little town, nestled on the banks of the Avon River is centrally located between the towns of Wolfville and Windsor. The second floor of this century home has been renovated into a cozy two bedroom apartment that would be a great place to come stay with your family or friends. All your amenities, such as grocery, pharmacy, liquor store, cafes are within walking distance. *Now featuring a private, outdoor sauna*

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.

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.