Holiday rentals in Greenwood

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Top-rated holiday rentals in Greenwood

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Top guest favourite
A wooden deck extends from the entrance, featuring potted plants and a barrel. The view includes lush greenery leading to the Bay of Fundy under a clear sky, with water visible in the distance. A gentle breeze sways the hanging bird feeders.
Cottage in Canning
4.96 out of 5 average rating, 139 reviews

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.

Superhost
Home in Kingston
4.84 out of 5 average rating, 158 reviews

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!

Top guest favourite
A modern kitchen area features white cabinetry, stainless steel appliances, and a countertop with two tall, curved stools. Natural light enters through sliding glass doors that lead to an outdoor deck, with a view of trees outside. A cozy chair with a geometric pattern adds warmth.
Guest house in Aylesford
4.98 out of 5 average rating, 174 reviews

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.

Superhost
An aerial view showcases the modern A-frame cottage enveloped by lush greenery. A spacious wooden deck extends from the home, featuring a cedar hot tub and various outdoor seating areas, providing an inviting space to enjoy the surrounding nature.
Cottage in Waterville
4.86 out of 5 average rating, 110 reviews

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!

Guest favourite
A single-story gatehouse is framed by mature trees displaying vibrant autumn foliage. The exterior is white, complementing the warm colors of the leaves. A gravel pathway leads to the entrance, enhancing the inviting atmosphere of the property.
Home in Aylesford
4.97 out of 5 average rating, 209 reviews

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.

Top guest favourite
Cottage in Margaretsville
4.89 out of 5 average rating, 144 reviews

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.

Top guest favourite
A hot tub is situated on a wooden deck with steps leading up to it. The water is bubbling gently, reflecting the warm hues of the sunset. A grassy field and trees are visible in the background, enhancing the serene outdoor setting.
Home in Kentville
4.98 out of 5 average rating, 431 reviews

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.

Top guest favourite
Home in Lunenburg
5 out of 5 average rating, 175 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.

Top guest favourite
A charming studio exterior is framed by vibrant flowers in full bloom. A yellow door welcomes guests, and a small patio with two chairs invites relaxation. The area is surrounded by greenery and a rustic wooden fence, enhancing the natural setting.
Guest suite in Melvern Square
4.98 out of 5 average rating, 160 reviews

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.

Top guest favourite
A wooden dock extends over calm waters, leading to two teal chairs positioned at the edge. Surrounding boulders and scattered rocks create a natural shoreline, with a distant tree-lined horizon visible across the lake's surface.
Cottage in Greenfield
5 out of 5 average rating, 195 reviews

The Harmony Grand at Molega Lake

Harbour Acres Cottages offering: 5⭐"The Harmony Grand". A private modern log cottage perched on the serene shores of Molega Lake; Nova Scotia's South Coast cottage country. Experience this two bedroom, full bathroom, kitchen, & living room lakefront accommodation for either a short overnight stay or a longer vacation. We cater to all travelers! Breakfast is included*

Top guest favourite
Loft in Berwick
4.93 out of 5 average rating, 131 reviews

Bay of Fundy 1BR Loft

Panoramic views of the Fundy. (The cliffs of Fundy has been designated UNESCO Global Geopark site) Inside or out feel like your on the water. Everything has been designed to please the traveler. Easy access all year round, a romantic getaway, a writers retreat, storm watching enthusiasts or a friends long weekend.Harbour villa west will make you want to return for more.

Top guest favourite
A deck features two Adirondack chairs positioned near a hot tub, surrounded by vibrant flowers. Lush green fields and trees are visible in the background, providing a serene and natural setting.
Cabin in Kingston
4.96 out of 5 average rating, 440 reviews

Bramble Lane Farm & Cottage

Enjoy wonderful views of trees and rolling fields from the deck of this beautifully renovated 100+ year old, post-and-beam constructed barn. Two open loft sleeping areas, two bathrooms, full kitchen, all linens and towels provided. Outdoor hot tub, barb-b-q, and ping pong table. Spacious yet cozy, comfortable, private and quiet.

Popular amenities for Greenwood holiday rentals

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