Holiday rentals in Greenwood

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

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!

Halls Harbour BEACH HOUSE Cottage w/Hot Tub

This restored seaside guest cottage is an ideal getaway place for couples. Wake up to the sound of the ocean's waves, and enjoy the beautiful sunsets in the private hot tub overlooking the Bay of Fundy. Take the stairs to the beach to beachcomb for treasurers. Prepare your own meals or enjoy a meal next door at the Halls Harbour Lobster Pound Restaurant. A great place to use as home base while exploring the Annapolis Valley, hiking to Cape Split or visiting the many local breweries and wineries.

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.

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.

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.

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

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.

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.

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.

Studio-like Comfort in Wolfville’s Beating Heart

This newly renovated studio-like private lower-level suite in the heart of Wolfville offers a compact sanctuary of order and warmth. Ideal for solo seekers or couples, it blends simplicity with comfort—steps from fine cuisine, boutique shops, and spirited conversation. Whether you're tasting wine, walking the dykes, or soaking in the cultural current, this is your perfect launchpad for meaningful adventure.

Bay of Fundy 1BR Loft

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.