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Holiday rentals in Annapolis

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Top-rated holiday rentals in Annapolis

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Top guest favourite
Cottage in Bridgetown
5 out of 5 average rating, 20 reviews

Rustic Riverside Retreat

Relax and enjoy our waterfront retreat that offers the perfect blend of modern elegance and rustic charm on the Annapolis River. Take in a stunning sunrise on the dock or unwind in the hammock listening to nature. For the adventurer try kayaking, hit the ATV trails on your bike or bring your fishing gear and give the river a try. Who knows, you might hook the big one! After a full day you can unwind by the firepit while admiring the starry sky or curl up by the fireplace with a cozy blanket.

Guest favourite
The exterior of the tiny house is illuminated by warm light emanating from the glass doors, highlighting its inviting entrance. The surrounding natural environment is visible in the dusk, with hints of trees and greenery blending into the evening sky.
Tiny home in Annapolis Royal
4.81 out of 5 average rating, 238 reviews

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.

Top guest favourite
A quaint seaside cottage is framed by vibrant flowering shrubs and greenery. The wood-paneled exterior features multiple windows and a distinctive yellow door. A set of adirondack chairs is situated on a wooden deck, and steps lead up to the entrance of the cottage.
Guest house in Centreville
4.95 out of 5 average rating, 309 reviews

Halls Harbour BEACH HOUSE Cottage w/Hot Tub

This restored seaside guest cottage is an ideal getaway place for couples. Wake up to the sound of the ocean's waves, and enjoy the beautiful sunsets in the private hot tub overlooking the Bay of Fundy. Take the stairs to the beach to beachcomb for treasurers. Prepare your own meals or enjoy a meal next door at the Halls Harbour Lobster Pound Restaurant. A great place to use as home base while exploring the Annapolis Valley, hiking to Cape Split or visiting the many local breweries and wineries.

Top guest favourite
A serene view of the water is framed by gently swaying grasses under a colorful sky at sunset. The open-concept layout of the kitchen and dining area is visible, showcasing a wooden dining table with six chairs, sleek cabinetry, and modern light fixtures.
Flat in Port Williams
4.99 out of 5 average rating, 170 reviews

NEW 2 Bed Amazing Views Port Williams Wolfville

Relax in this calm, stylish space located in the heart of beautiful Port Williams! This bright, newly-renovated private unit offers plenty of space and natural light with sensational views of the Annapolis Valley. Just a quick five minute drive to Wolfville with easy access to the 101 highway. This luxury 2 bedroom upper unit is less than a two minute walk to outstanding local pubs and restaurants. it’s a perfect spot to explore the many wineries and craft breweries nestled across the valley.

Top guest favourite
The A-Frame chalet is shown from the lakefront, featuring large wall-to-wall windows that reflect the serene lake view. A wrap-around deck is visible, complemented by outdoor seating. The natural surroundings enhance the rustic charm of the wooden structure.
Chalet in Church Point
5 out of 5 average rating, 139 reviews

At the Ford du Lac

In the rural Acadian community of Clare, you will find our fully equipped, recently updated, 1 bedroom + loft A-Frame style chalet sitting on a quiet lake. The beautiful view can be enjoyed from wall to wall windows, wrap around deck, or while sitting in the hot tub. Loft: 1 king & 1 single bed - excellent for traveling with children. Downstairs bedroom: 1 queen bed. Living room: double pull out sofa & futons. We live next door so let us know if anything is missing during your stay!

Top guest favourite
A serene lakeside view is captured with sunlight glistening on the water. The beach is lined with gentle waves, and a wooden dock is visible leading into the lake. A railing runs along the deck where seating is provided, set against lush greenery.
Cottage in Middleton
4.93 out of 5 average rating, 89 reviews

Serene lakefront living. Two bedroom cottage.

Relax with the whole family at this peaceful paradise on Trout Lake, New Albany, NS. Enjoy magical sunsets from the large lakeside patio, comfortably furnished screen room or firepit. Take in the scenery via kayaks, paddle boat or bicycles. A quick float or a short walk with water shoes will take you to a swimming area with a floating dock complete with cup holders & reclining seats. BBQ & full kitchen on site. WiFi, Sat TV, & outside/inside games provided for your entertainment.

Top guest favourite
Two individuals are seated comfortably in wooden adirondack chairs on a deck, overlooking a serene body of water. A small table holds two glasses of water, with the sun setting in the background, illuminating the scene with a warm glow.
Flat in Annapolis Royal
5 out of 5 average rating, 137 reviews

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.

Top guest favourite
A Highland cow is prominently featured in the foreground, showcasing its long horns and distinctive orange-brown fur. The animal stands in a grassy field with trees and a blue sky in the background, reflecting the farm landscape of The Owl's Nest Wilderness Cottage.
Farm stay in Clementsvale
4.98 out of 5 average rating, 106 reviews

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.

Guest favourite
A modern loft-style unit is shown at dusk, illuminated by large windows. A wooden deck extends outdoors, featuring two blue adirondack chairs. The surrounding grassy area is sparse, indicating recent landscaping. The structure showcases clean lines and a contemporary design against a cloudy evening sky.
Townhouse in Berwick
4.94 out of 5 average rating, 121 reviews

Bayfront 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.

Top guest favourite
An open-concept kitchen and dining area features wooden beams and light-colored walls. A spacious kitchen island is surrounded by stools, while a dining table is positioned for gatherings. A comfortable gray sofa is located nearby, contributing to the relaxed atmosphere.
Barn in Smiths Cove
4.99 out of 5 average rating, 443 reviews

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)

Top guest favourite
The cottage features a spacious porch with wooden deck chairs overlooking a serene lake. A peaceful waterfront landscape is framed by a neatly manicured lawn, with natural stone accents leading down to the water's edge.
Cottage in Annapolis, Subd. D
4.96 out of 5 average rating, 112 reviews

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 when you're not exploring Nova Scotia. End your days relaxing by the fire pit or by sipping your favourite drink on the front deck overlooking the lake and taking in the dark sky preserve.

Top guest favourite
Home in Lunenburg
5 out of 5 average rating, 148 reviews

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.

Popular amenities for Annapolis holiday rentals