Holiday rentals in Greenwood

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Top-rated holiday rentals in Greenwood

Guests agree: these stays are highly rated for location, cleanliness and more.

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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.
Guest house in Aylesford
4.98 out of 5 average rating, 178 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
A blue single-story house is set within a lush green lawn, surrounded by trees. A picnic table is positioned nearby on the grass, offering a space for outdoor gatherings. The home features a white door and a window, framed by landscaping that enhances the natural setting.
Guest suite in Middleton
4.99 out of 5 average rating, 103 reviews

Elegant home away from home - Valley View

Away from it all and under the stars. This modern unit offers a relaxing, quiet experience. Conveniently located just off Hwy 101, close to amenities and the famous Bay of Fundy (highest tides in the world). Enjoy your own semi-private space in our backyard with a stunning view of the valley. See the sunrise while sipping your coffee, splash in the pool on hot days and have your BBQ at the picnic table. Look at the stars while the firepit keeps you cozy or snuggle up inside on those rainy days.

Top guest favourite
A restored cabin features a private hot tub on the deck, surrounded by greenery. Soft evening lights illuminate the exterior, highlighting the weathered wood and shingles. Nearby, colorful houses add a charming backdrop, with the setting sun casting a gentle glow over the scene.
Guest house in Centreville
4.95 out of 5 average rating, 106 reviews

Halls Harbour BOAT HOUSE Cottage w/Hot Tub

This seaside heritage cabin is an ideal getaway place which has welcomed more than 1000 guests since 2017. Wake up to the sound of the ocean waves and enjoy beautiful sunsets while relaxing in the hot tub overlooking the Bay of Fundy. Take the steps to the beach and beachcomb for treasures. Prepare your own meals or enjoy a meal next door at the famous Lobster Pound Restaurant. Experience the Annapolis Valley, including visiting wineries, hiking Cape Split or watching the world's highest tides!

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
4.96 out of 5 average rating, 46 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.

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
4.87 out of 5 average rating, 112 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, 215 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
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
4.93 out of 5 average rating, 280 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.

Guest favourite
Home in Aylesford
4.88 out of 5 average rating, 8 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, 441 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, 162 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.

Top guest favourite
The exterior of a charming barn-style cottage is framed by vibrant pink flowers and lush green grass. Tall trees provide a natural backdrop, while a lantern adds a warm touch to the garden scene. The cottage features a gray shingled façade with yellow accents.
Cabin in Kingston
4.96 out of 5 average rating, 442 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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