Holiday rentals in Greenwood

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!

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.

Ocean Front #2 HotTub 2 bdrm Rooftopdeck BBQ 2bath

Escape to Oceanfront Bliss! This stunning property features an epic deck, perfect for sunbathing or evening gatherings. Step inside to discover modern finishes a blend style & comfort soak in a hot tub with ocean views. Rooftop deck for stargazing& Sunsets! The luxurious King Master suite with an ensuite and a cozy queen bedroom provide ample space for family and friends. Experience the ultimate lifestyle of relaxation, where every moment is a celebration, create memories. Book your stay now!

Fern-Gran Fundy Cottage on the Bay of Fundy

This cottage, with spectacular views of the Bay of Fundy and the most breathtaking sunsets, was fully renovated in 2021. The cottage has 2 bedrooms, an open living/kitchen area and a full bath. Large deck with BBQ, table and chairs. Beach access is only a few minutes walk away where you can walk for hours or sit and watch the highest tides in the world or if you prefer to be inside, a smart tv is ready for your streaming accounts. Wineries, historic sites & amazing hike locations are close by.

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.

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.

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.

TideWater Suites 2 Bedroom

Modern 2 bedroom, 2 bathroom, loft style unit on a 4 acre lot with unbelievable views located on cliffs of the Bay of Fundy. (The cliffs of the Bay of Fundy has been designated a UNESCO Global Geopark site) Just a short few minutes away Harbourville beach, restaurant and fish market (open during fishing season). Berwick is 20 mins away and has all the amenities you may need. Vacation in style and enjoy your views of the highest tides in the world.

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.

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*

Eagles Nest Retreat - Oceanside cottage

Escape the ordinary and relax in our quaint, rustic cottage with private beach, directly in front of the legendary Five Islands along the Glooscap Trail. This area is Canada's newly proclaimed UNESCO Global Geopark. Be mesmerized by the dramatic (and world's highest) Bay of Fundy tides during the day and the stars overhead at night - all right at your doorstep.

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.