Vacation rentals in Middleton

A-Frame by the Bay

Slow down and soak up the beauty of the Bay of Fundy at this oceanfront A-frame in Scots Bay. Just steps from the shore and a 5-minute walk to the Cape Split trailhead, it’s perfect for hiking, paddling, and relaxing by the water. Sleeps up to 5 with cozy, coastal charm. Enjoy beach fires, dramatic tides, and local gems like Saltair Nordic Spa (25 mins), The Long Table Social Club, and award winning Valley wineries & breweries (20-40 mins). A peaceful place to reconnect with nature—and yourself.

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.

Nova Scotia A-Frame with Hot Tub

Welcome to the Nova Scotia A-Frame! This striking cottage is located in Aylesford Lake, Annapolis Valley. Over 3 years, the a-frame has been developed with immense passion and a keen eye for detail. Exuding relaxing vibes, the organic neutral tones inside allow you to fully absorb the natural surroundings. Enjoy a morning soak in the cedar hot tub followed by yoga on the top deck. Fine dining at a nearby vineyard, then a glass of wine by the wood stove. You've just found your next getaway!

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.

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!

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.

Peaceful Central Valley home w/ CalmGardens&wifi

This peaceful home comes with amenities such as Wi-Fi and your first day free coffee/ and tea . The Keurig machine is a K Cup and Carafe maker. If you want to go to restaurants, shops, and cafes, we're within walking distance. Tim Hortons a short drive away. In the heart of the fabulous Annapolis Valley. It will enchant you with its unique charm. Shop the local fruit markets, antique shops, and craft stores. Golf nearby. A Short drive to the wineries and the Bay of Fundy.

Romantic getaway with a view double jacuzzi tub.

Take it easy at this unique and tranquil getaway. View The Annapolis Valley in the 40ft. sunroom or enjoy the changing tides of the Minas Basin. Relax in the 2 person jet tub after a hike to Cape Split or near by beaches Snuggle in front of the fireplace for a romantic evening. A seasonal restaurant and Look Off Park is located just a short walk away or if you prefer to cook we have a few small cooking appliances. Microwave, Hotplate oven, BBQ everything you need.

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.

Hot Tub Retreat | Valley Views | Near Kentville AC

Welcome to “The Twelve,” a luxury 2-bedroom retreat set privately in the Annapolis Valley, just 15 minutes from Wolfville. Perfectly located for exploring the region’s wineries and craft breweries, this stylish home offers a relaxing and elevated getaway. Step into a bright, open-concept space with a modern kitchen and peaceful valley views. Unwind in the private hot tub with your favourite wine, or take in beautiful sunrises and sunsets from the deck.

Ocean Front #3 HotTub Sunset RoofTopDeck BBQ 2bath

Waterfront Cottage: Huge deck, sun sets, Private Hot Tub: 6 Person tub for 2. Panoramic Water Views: Modern Cabin: privacy and a peaceful environment. Large Deck: outdoor living space both you can take in the sun or retreat into the share. Nature Retreat with wildlife Romantic Escape: for couples, Heated floors, Shower tower, queen master, an extra guest could sleep on the couch. Super private chefs kitchen. Well equipped for all seasons.