
Holiday houses in Annapolis
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Top-rated holiday rentals in Annapolis
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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.

Cozy, Spacious Cottage on Peaceful Property
This cozy cottage nestled in quiet Granville Beach is close enough to all amenities of Annapolis Royal, but tucked away into a serene property surrounded by greenery with a view of the river. This cottage comes with everything you need and more, a fully functional kitchen with stove/ oven, mini fridge, microwave and sink. A bathroom with toilet and shower and a comfy living space, just outside of the bedroom separated by a sliding door. This is the perfect place to have a house away from home.

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!

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.

Oceanfront Oasis
We are proud to offer you a luxurious vacation experience in our registered heritage building. The oldest commercial property in Annapolis Royal offers you all the modern conveniences that vacationers expect. Located in the heart of Annapolis Royal, recognized by MacLean's Magazine as one of the "10 PLACES YOU'VE GOT TO SEE" in Canada. Within walking distance you can dine in cafes, pubs and fine dining establishments. Live theatre, a farm market and national parks are nearby.

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.

The Barn at Lazy Bear Brewing
Stay at Lazy Bear Brewing. We have a unique retreat waiting for you above our brewery. A one-bedroom, newly renovated apartment with a private deck to enjoy the sunset over the Digby Gut. You may even enjoy it with our Gut View Amber Ale! We're located in the quiet village of Smith's Cove, a short walk to a sandy beach, and five minutes to shopping, entertainment and restaurants in Digby. Complimentary growler of beer upon arrival (must be 19)

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.

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.

Studio-like Comfort in Wolfville’s Beating Heart
This newly renovated studio-like private lower-level suite in the heart of Wolfville offers a compact sanctuary of order and warmth. Ideal for solo seekers or couples, it blends simplicity with comfort—steps from fine cuisine, boutique shops, and spirited conversation. Whether you're tasting wine, walking the dykes, or soaking in the cultural current, this is your perfect launchpad for meaningful adventure.

Entire private homey apartment Saint John West
Bright, spacious apartment on Saint John's West Side, within walking distance to Bayshore Beach and Martello Tower, and just minutes from the Digby-Saint John ferry, Irving Nature Park, and downtown. Enjoy nearby restaurants, shops, and trails. This newly renovated upstairs duplex features two bedrooms with 2 queen beds and a living room, comfortably accommodating up to 4 guests.
Popular amenities for Annapolis holiday rentals
Other great holiday rentals in Annapolis

Tanglewood Cabin

Elegant home away from home - Valley View

Nova Scotia A-Frame with Hot Tub

Cute Unit on Markland

Paradise Coach House/Maisonette à Paradise

Carolina Hideaway

The Loft in Annapolis Royal

The Sea Shanty
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