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Holiday houses in Greenwood

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Top-rated holiday rentals in Greenwood

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Top Guest favourite
Cottage in Canning
4.96 out of 5 average rating, 135 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
The living area features a gray sofa and an armchair, complemented by a wooden coffee table. A floor lamp provides soft lighting beside a window. The space is designed with a light color palette and has a fan mounted on the ceiling.
Home in Kingston
4.84 out of 5 average rating, 153 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 well-appointed bedroom features a spacious bed with striped bedding and accent pillows in rich colors. Soft bedside lamps provide warm lighting, while natural light enters through two windows framed by light curtains. A small nightstand complements the inviting atmosphere.
Guesthouse in Aylesford
4.98 out of 5 average rating, 170 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.

Guest favourite
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
4.88 out of 5 average rating, 105 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, 208 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
An aerial view showcases a serene cottage nestled among lush greenery, with trees lining the path leading to the property. The bay stretches in the background, offering a stunning view of the water and distant shores.
Cottage in Centreville
4.98 out of 5 average rating, 207 reviews

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!

Top Guest favourite
The exterior of a charming blue century home is depicted, showcasing a welcoming covered porch with white railings. Large windows are present on the upper floor, and the entrance features a red door. Lush greenery surrounds the property, enhancing its inviting appearance.
Apartment in Hantsport
5 out of 5 average rating, 163 reviews

Historic East Coast Apartment *Private Sauna*

On your next valley get away, stay in charming Hantsport. This endearing little town, nestled on the banks of the Avon River is centrally located between the towns of Wolfville and Windsor. The second floor of this century home has been renovated into a cozy two bedroom apartment that would be a great place to come stay with your family or friends. All your amenities, such as grocery, pharmacy, liquor store, cafes are within walking distance. *Now featuring a private, outdoor sauna*

Top Guest favourite
A charming cottage is perched on stilts amidst lush green foliage. Large windows provide expansive views, allowing natural light to fill the space. The surrounding landscape features a blend of trees and grass, creating a peaceful and serene atmosphere.
Cottage in Margaretsville
4.89 out of 5 average rating, 142 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 sun-filled sunroom showcases a mix of comfortable seating arrangements, including wicker chairs and a coffee table. Large windows provide expansive views of the surrounding landscape, while potted plants add a touch of greenery to the inviting space.
Guest suite in Canning
4.92 out of 5 average rating, 256 reviews

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.

Top Guest favourite
A hot tub is situated on a wooden deck, with steam rising gently from the water. The background features a serene view of rolling hills under a colorful sunset, creating a peaceful setting for relaxation.
Home in Kentville
4.98 out of 5 average rating, 418 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
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
4.97 out of 5 average rating, 156 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.

Superhost
A single-story residence is surrounded by manicured lawns and tall trees. A combination of white siding and brick accents decorates the facade. A screened-in porch is visible on the right side, offering a glimpse of indoor-outdoor living.
Home in Kingston
4.81 out of 5 average rating, 48 reviews

Home Away From Home in Kingston, NS

Welcome to Kingston, Nova Scotia! This charming home comfortably sleeps six. Has laundry, screened area with dining set & side patio with BBQ. A perfect hub just mins to military base or walk to park, hockey rink, schools & groceries. The proximity to a craft brewery and cafe adds to the local charm. Easily accessible near Exit 17 Hwy 101 it’s a breeze to reach your destinations. Enjoy a seamless and enjoyable stay.

Popular amenities for Greenwood holiday rentals

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  4. Kings County
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