Holiday houses in Middleton

Cozy Victorian Tiny Home in Tree Oasis

Only 6 mins from historical Annapolis Royal. Last minute/same day bookings always welcome. Once used for horse carriages, I converted this into a private, 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, beyond ballpark, perfect for cycling into town.

Value · Location · Quiet

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!

Location · Value · Heating

Ocean Front #2 HotTub 2 bdrm Rooftopdeck BBQ 2bath

Escape to Oceanfront Bliss! This stunning property features an epic deck, perfect for sunbathing or evening gatherings. Step inside to discover modern finishes a blend style & comfort soak in a hot tub with ocean views. Rooftop deck for stargazing& Sunsets! The luxurious King Master suite with an ensuite and a cozy queen bedroom provide ample space for family and friends. Experience the ultimate lifestyle of relaxation, where every moment is a celebration, create memories. Book your stay now!

Value · Family · Outdoor spaces

Van’s house with view of fields and Bay of Fundy

Enjoy this serene space immersed in nature. Van’s house, with 38 acres of fields, overlooks the Bay of Fundy from N. Mountain (600’ elev.). Swimming lake is 1/2 mile away. There is one small bedroom with queen bed, and living room has sliding door to create 2nd bedroom with pull out full futon. Kitchen/dining room has lots of counter space/ no dishwasher. One full bathroom with tub/shower. Washing machine/ no dryer (clothesline and rack are provided). Only 1st floor accommodations available.

Location · Wi-Fi · Nearby

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.

Family · Location · Laundry

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!

Location · Value · Amenities

The Star Dome at the Belleisle Bayview Retreat!

We offer one night stays! Enjoy stunning panoramic sunset views of the beautiful Belleisle Bay in the Star Dome; situated in a natural meadow near the lodge building. The Star Dome provides a unique experience with propane fireplace, and a clear roof for star gazing. The outdoor viewing deck includes a kitchen with all utensils/ hot sink, hot shower, toilet and BBQ. Round out your relaxation with our Finnish wood-stove sauna and cold tub at $50 per hour.

Value · Family · Checkout

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.

Family · Location · Check-in

Country Inn by the Bay - Chalet

A European style country inn, restaurant and 63 acre forest OPEN YEAR ROUND, just 1 km from the Bay of Fundy. Surround yourself with the comfort of nature in this quaint, cozy tiny house known as The Chalet. Unique features are the sauna, wood stove and kitchenette. In the morning, a European style continental breakfast is served in the guest lounge. Enjoy this hearty breakfast on the large deck with other guests or in the privacy of the chalet.

Location · Value · Beach

TideWater Suites 2 Bedroom

Modern 2 bedroom, 2 bathroom, loft style unit on a 4 acre lot with unbelievable views located on cliffs of the Bay of Fundy. (The cliffs of the Bay of Fundy has been designated a UNESCO Global Geopark site) Just a short few minutes away Harbourville beach, restaurant and fish market (open during fishing season). Berwick is 20 mins away and has all the amenities you may need. Vacation in style and enjoy your views of the highest tides in the world.

Value · Family · TV

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.

Value · Family · Hospitality

Eagles Nest Retreat - Oceanside cottage

Escape the ordinary and relax in our quaint, rustic cottage with private beach, directly in front of the legendary Five Islands along the Glooscap Trail. This area is Canada's newly proclaimed UNESCO Global Geopark. Be mesmerized by the dramatic (and world's highest) Bay of Fundy tides during the day and the stars overhead at night - all right at your doorstep.

Location · Value · Condition