Holiday houses in Greenwood

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Top-rated holiday rentals in Greenwood

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Superhost
A round swimming pool is surrounded by a wooden deck and shaded by trees. A gazebo is visible nearby, and pool steps lead into the clear water, reflecting sunlight. The serene outdoor setting emphasizes a relaxed atmosphere.
Loft in Kentville
4.83 out of 5 average rating, 385 reviews

Winemakers Inn

We are offering a upstairs guest suite in our home in the beautiful Annapolis Valley. We live in a quiet neighborhood minutes from Kentville ,New Minas ,Wolville. We have a pool and deck with a BBQ in season that we will share. We are close to popular hiking / snowshoeing trails ,wineries and shopping. We are within walking distance of Valley Regional Hospital .We are not set up for long term living. Any questions message me. Enjoy your stay. Our cats name is peanut she is out side a lot

Superhost
A two-story house features a light blue exterior with white accents. A covered front porch is supported by wooden posts, with a few steps leading to the entrance. A satellite dish is mounted on the side, while trees provide a natural backdrop.
Home in Kingston
4.84 out of 5 average rating, 145 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.
Guesthouse in Aylesford
4.98 out of 5 average rating, 161 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 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
4.99 out of 5 average rating, 212 reviews

The Loft

Welcome to The Loft! Winter rate discount Jan -March. 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.

Top Guest favourite
Apartment in Kentville
4.94 out of 5 average rating, 395 reviews

New Upgrade The Rustic Oasis (Coldbrook/Kentville)

UPGRADED/BIGGER SPACE located in the Annapolis Valley. This flat is a beautiful escape whether it be business or pleasure it has all the needs of home.Sleeps 6 quests with 2 double beds and a fold down comfy futon.Electric fire place.Full kitchen, coffee, bbq, patio, washer & dryer. (see full amenities). Digital cable, Smart TVs, Wifi and Netflix provided.Mins away from the #1 Hwy, and the #101 Hwy to all towns, and tourism needs.5 min drive to the hospital for personal or professional stay.

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, 203 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 exterior of a cottage is surrounded by lush greenery and features a circular swimming pool. Colorful flowers and shrubbery line the walkway, leading to wooden lounge chairs and a shaded umbrella. A fire pit area is visible, inviting outdoor gatherings.
Tiny home in Nova Scotia
4.97 out of 5 average rating, 247 reviews

Cozy Cottage on South Shore. 30 min from Halifax!

A very cozy and peaceful place to base any vacation on the South Shore out of. Very close to hiking and ATV trails. No visible neighbors from the yard, lots of wildlife. Large parking areas. Interior is a mixture of new and re purposed materials. Appliances are small but functional, all the comforts of home but smaller. Double bed is incredibly comfortable. It is my home that I vacate for guests, and contains some sentimental decorations and items. RYA-2023-24-03271525339628999-1197

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
An open living space features a comfortable sofa and a dark wood dining table surrounded by four chairs. A large window allows natural light to illuminate the room. A television is positioned on a black entertainment unit, contributing to a relaxed atmosphere.
Apartment in Kentville
4.93 out of 5 average rating, 143 reviews

Casa Young I - Kentville Suite

Casa Young is a fully-furnished, accessible, upper-level suite located in the Town of Kentville, only steps away from the Valley Regional Hospital. The private driveway provides ample parking and access to one of the two private entrances, including a wheelchair ramp. The home is located within walking distance to the Harvest Moon trail, bike paths, sports arena, tennis courts, swimming pool with splash pad, playgrounds, and also many nearby restaurants, cafes, and pubs.

Superhost
The exterior of a detached garage is shown, featuring a two-car capacity with modern glass doors. The upper section displays a triangular roof with shingle accents and a small, horizontal window. Surrounding greenery and a gravel driveway enhance the natural setting.
Guest suite in Kentville
4.84 out of 5 average rating, 102 reviews

Studio loft in Annapolis Valley

*** New heat pump added December 2023 The loft is centrally located close to many hiking trails, grocery, restaurants and shops downtown. The loft is a short drive to many of the Annapolis Valley highlights like wineries, Wolfville, Blomidon, Grande Pre and many others. While visiting you will enjoy a separate building from the main house with outdoor parking. The loft includes a 3-piece bathroom, kitchenette with fridge and freezer, TV, WIFI and streaming services.

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, 149 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
Apartment in Port Williams
4.96 out of 5 average rating, 444 reviews

Port Williams 2 Bed Beautiful Bright Wolfville A/C

Located in the heart of beautiful Port Williams, this bright, newly-renovated private unit offers plenty of space and natural light. This modern, stylish two-bedroom unit is (less than a two minute walk!) to outstanding local pubs and restaurants such as The Noodle Guy, The Port Pub & Bistro, The Port Taproom and Bay of Fundy Brewing. The location is a quick five minute drive to Wolfville with easy access to the 101 highway.

Popular amenities for Greenwood holiday rentals

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