Holiday houses in Greenwood

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Top-rated holiday rentals in Greenwood

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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, 159 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, 175 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.

Top Guest favourite
An open living/dining area features a sofa accented with a throw blanket. A wooden coffee table and a dining table with chairs sit under natural light, flowing through double doors that open to the outdoor space. Neutral tones create a calming atmosphere.
Guest suite in Aylesford
4.95 out of 5 average rating, 44 reviews

Farm Stay - 1 bedroom suite on rural farm property

If you're looking for peace and tranquility, you will find it here. Located on a quiet dirt road with lots of land, you will be able to sit back and enjoy the sounds of nature. This newly renovated suite offers stunning views of the Annapolis valley, and access to our beautiful property with fields, ponds, and forest that you're free to explore. Enjoy a soak in our spacious claw foot soaker tub at the end of the day, or just curl up in your comfy king sized bed and enjoy the peace & quiet.

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
4.86 out of 5 average rating, 111 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, 213 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
The cabin's exterior is framed by trees, illuminated by warm interior lights that reflect off large windows. A spacious wooden deck is visible, featuring two red chairs positioned towards the inviting entrance. The structure showcases a triangular gabled roof and a charming mix of wood siding.
Cabin in LaHave
4.97 out of 5 average rating, 913 reviews

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!

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, 117 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.

Top Guest favourite
A cozy living space is presented with a spacious bed and a comfortable seating area. A small dining table is set for two, adorned with decorative plates. Natural light fills the area through a window, illuminating the modern kitchenette and accent decor.
Guest suite in North Alton
4.98 out of 5 average rating, 221 reviews

The Loft

Welcome to The Loft! This is a private second floor unit. The Loft is available year around. We are located on a beautiful golf course with beautiful views. We offer private independant living with your own private entrance. Unit does not have a stove it does have lots of kitchen gadgets to make almost any meal. There are no added cleaning fees. Close to hospital,Kentville,Coldbrook and New Minas. Minutes off of the 101 exit 13.Clean, modern and safe units.

Guest favourite
Home in Aylesford
4.86 out of 5 average rating, 7 reviews

Storybook Craftsman Cottage - Annapolis Valley

Charming 3-bedroom, 2-bath Craftsman-style retreat in Aylesford, Nova Scotia. Set amid beautiful, established gardens, this home blends warmth, character, and timeless charm. A screened back porch offers the perfect place to relax and enjoy the peaceful surroundings year-round. Filled with natural light and inviting living spaces, it captures a storybook feel reminiscent of rural Nova Scotia living. A true retreat full of charm, comfort, and quiet beauty.

Top Guest favourite
Home in Kentville
4.98 out of 5 average rating, 435 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
4.98 out of 5 average rating, 161 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 modern villa is illuminated at night, featuring large glass windows that provide expansive views. The structure is set on a grassy slope, with outdoor seating and a grill visible on the patio, enhancing the outdoor living space.
Townhouse in Berwick
4.93 out of 5 average rating, 131 reviews

TideWater Suites 1 Bedroom

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.

Popular amenities for Greenwood holiday rentals

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