Vacation rentals in Middleton

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Top-rated vacation rentals in Middleton

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Guest favorite

A garden area features vibrant purple irises and lush green hostas surrounding a circular flower bed. The space is bordered by light-colored bricks, enhancing the natural beauty of the plants. Soft grass lies adjacent, providing a serene and inviting outdoor environment.

Loft in Kentville

4.84 out of 5 average rating, 317 reviews

Winemakers Inn, Newly renovated guest suite.

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

Guest favorite

A wicker basket is positioned in a corner, containing two soft tan pillows and a textured cream throw blanket draped over the side. The hardwood floor adds warmth to the setting, while the minimalist design provides a sense of comfort and relaxation.

Home in Kingston

4.92 out of 5 average rating, 114 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 favorite

A modern living space features exposed wooden beams above and a combination of gray and white furnishings. A cozy sofa is paired with a coffee table, while a dining table with four chairs is positioned nearby. Kitchen amenities include a refrigerator and a stove, enhancing convenience.

Guest suite in Middleton

4.98 out of 5 average rating, 46 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 favorite

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

4.97 out of 5 average rating, 140 reviews

Mid Valley Suite

This new 2 bedroom guesthouse, centrally located in the beautiful Annapolis Valley, is 5 minutes from the famous Oaklawn Farm Zoo; Berwick, Apple Capital of NS, is 8 minutes from us; Greenwood Air Force Base is 15 minutes away. Explore the Valley from end to end -- Wolfville, home of Acadia University and vineyards is a half hour away, while at the other end of the Valley is Annapolis Royal, the first European settlement in North America. Peggy's Cove, Lunenburg, Digby are all an easy drive.

Top guest favorite

A bright living area features a leather sofa with decorative pillows, paired with a curved glass coffee table. Natural light filters through sheer curtains of a nearby window, while a floor lamp provides additional lighting. A colorful artwork adds visual interest to the space.

Home in Aylesford

4.98 out of 5 average rating, 184 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.

Guest favorite

A well-equipped kitchen features blue cabinetry and marble countertops. Open shelves display various dishes and decorative items. A window provides natural light, while appliances, including a dishwasher and a stove, are neatly arranged. A patterned rug adds texture to the tiled floor.

Home in Annapolis Royal

4.95 out of 5 average rating, 110 reviews

Holiday House

Hello and welcome to the holiday house at Hummingbird Hill! Conveniently located between exits 21 and 22 off the 101 hwy, we are the ideal location for travelers looking to cross on the Digby ferry. This single level house has all the necessary amenities and is accessible to all. Our large property boasts gardens, fire pits, and yard games. The Rosette forestry trail is also open to all visitors of humming bird hill. We hope you will join us in our little piece of paradise.

Guest favorite

A rocky shoreline is visible, featuring a variety of textures and colors in the stones, with the calm, grey waters of the Bay of Fundy seen in the distance. The overcast sky reflects soft light onto the landscape.

Tiny home in Middleton

4.95 out of 5 average rating, 55 reviews

Cozy, 1-bedroom tiny home by the Bay of Fundy

NS Registration # STR2526A9960 Recently converted from a one-room bunkhouse, this tiny home is ready for a single person or a couple looking for a quiet getaway. Grocery stores, pharmacy, bank, restaurants, day spa, pub, liquor store and post office are a 10-minute drive away in Middleton. Enjoy breakfast, a book, and/or yoga on the private, shaded deck. Want a day trip? Whale-watch off Brier Island; kayak in Kejimkujik National Park; visit a winery, craft brewery, a zoo.

Guest favorite

Cottage in Margaretsville

4.89 out of 5 average rating, 116 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.

Guest favorite

The charming two-story home features a welcoming front porch and a gabled roof. Lush green trees surround the property, providing shade. A gravel pathway leads to the entrance, and a red vehicle is visible in the driveway. The landscape includes decorative plants and bushes.

Home in Middleton

4.96 out of 5 average rating, 45 reviews

Peaceful Central Valley home w/ CalmGardens&wifi

This peaceful home comes with amenities such as Wi-Fi and your first day free coffee/ and tea . The Keurig machine is a K Cup and Carafe maker. If you want to go to restaurants, shops, and cafes, we're within walking distance. Tim Hortons a short drive away. In the heart of the fabulous Annapolis Valley. It will enchant you with its unique charm. Shop the local fruit markets, antique shops, and craft stores. Golf nearby. A Short drive to the wineries and the Bay of Fundy.

Guest favorite

A gentle waterfall cascades over dark rocks, surrounded by vibrant greenery and rocky terrain. Sunlight reflects off the water, creating a shimmering effect. Various sizes of stones and pebbles are scattered along the riverbed, with lush foliage framing the scene.

Loft in Berwick

4.92 out of 5 average rating, 113 reviews

Stunning One BR Loft over looking the Bay of Fundy

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 favorite

A view from above captures the open loft layout of the barn. Sturdy wooden beams and warm wood paneling create an inviting atmosphere. A staircase ascends to the loft, while a comfortable seating area is visible below, featuring a recliner and a dining space in the distance.

Cabin in Kingston

4.95 out of 5 average rating, 376 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.

Guest favorite

The still water reflects a vibrant sunset, casting warm orange and pink hues against the silhouette of trees along the shoreline. The scene conveys a serene atmosphere, with gently rippling water and a peaceful sky transitioning from day to night.

Cabin in New Albany

4.86 out of 5 average rating, 111 reviews

Lakefront Cottage on Lake Zwickers

Retreat and relax in this rustic cottage on quiet Zwickers Lake. This lakeside cottage on the beach is ideal for a romantic getaway or family vacation. Feed our free range chickens, enjoy a paddle in the kayaks, canoe or pedalboat, and let the kids play in the sand with the many beach toys.

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Other great vacation rentals in Middleton

Guest favorite

A cozy outdoor area is presented with two wooden chairs placed near a circular fire pit, surrounded by lush greenery. The cottage is visible in the background, featuring a spacious deck and multiple trees providing shade.

Cottage in Granville Ferry

5 out of 5 average rating, 16 reviews

Pine Tree Cottage

SandraRating, 5 stars9 months ago

We were looking for a quiet place near Annapolis Royal yet out-of-town, and we found it. The trips to surrounding towns, restaurants, and tourist sites were easy and there was little traffic. Although not all the rooms in the cabin have been fully renovated yet, Patrick thoughtfully provided comfortable furnishings, and there were many 'homey' touches that we appreciated, like adequate lighting in each room, good quality linens and towels, and flowers on the table. We enjoyed the well-supplied kitchen, great shower, and deck for relaxing, outdoor breakfasts, and views of Milbury Lake from the private beach. Patrick was a responsive host and made sure we arrived safely and had everything we needed.

Top guest favorite

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, 118 reviews

Whispering Oaks Studio

AnnyRating, 5 stars1 week ago

Gareth’s cabin is such a perfect getaway! Everything you could want is there, and you can tell he really cares about his guests and their comfort because every suggestion I saw in the guest book had already been implemented by the time I visited! I highly recommend booking this suite for your next visit to the area.

Guest favorite

Tiny home in Annapolis Royal

4.78 out of 5 average rating, 165 reviews

Cozy Victorian Tiny Home in Tree Oasis

GregRating, 5 stars1 day ago

Although this is a “tiny house” the place is quite spacious and inviting. Room to work at the desk, lounge on the sofa, comfortable bed to sleep in. I appreciated Robert’s suggestion to try Annapolis Bay Area (I was going to drive to Digby) and the town was quite lovely with good restaurants. (I managed to squeak in at a busy place with a last minute reservation.) All in all a lovely stay! Thanks!

Guest favorite

A living area features large glass doors that open to a deck with ocean views. Natural light floods the space, illuminating comfortable seating options. The decor includes a cozy armchair and a coffee table positioned on a soft rug, with a warm color palette enhancing the seaside ambiance.

Cottage in Berwick

4.89 out of 5 average rating, 152 reviews

Seaside Escape - Wake to Waves & Panoramic Views

SamanthaRating, 5 stars2 weeks ago

Beautiful view. Road leading to the cottage is very bumpy but if you drive slow it’s ok. No service but has wifi just need to be careful that you start your GPS before leaving the cottage so you know where you’re going. 10/10 stay

Superhost

The rustic log chalet is set against a backdrop of vibrant blue skies and fluffy clouds. The charming exterior features natural wood detailing, multiple gabled roofs, and several skylights, creating a welcoming atmosphere in a serene landscape overlooking the water.

Home in Middleton

4.71 out of 5 average rating, 24 reviews

Your Rustic Ocean Chalet Escape

TristanRating, 5 stars2 weeks ago

Beautiful location, fantastic cottage . Couldn't ask for a better place to stay. Hidden gem.

Guest favorite

A sunset view over the ocean is captured, with warm hues of orange and pink illuminating the horizon. Silhouetted trees stand tall in the foreground, while a grassy area extends toward the water, framed by a fence in the distance.

Cottage in Aylesford

4.92 out of 5 average rating, 97 reviews

Bay of Fundy cottage

JoanneRating, 5 stars3 weeks ago

Jessica’s cottage was lovely with beautiful views! The cottage was very clean and had everything you need for a wonderful stay! We would definitely visit again!

Top guest favorite

Home in Bridgetown

4.97 out of 5 average rating, 35 reviews

Mountain View Sunsets Bungalow

DrewRating, 5 stars4 weeks ago

This place is wonderful to stay in. The patio offers a beautiful view, and there’s ample outdoor space. When the weather turns chilly, the fireplace keeps things cozy. The inside is spotlessly clean and well-equipped with everything you need. Our host was very pleasant to deal with, and all the instructions were clear and easy to follow. It’s conveniently located near the sports hub. We would definitely consider staying here again when we visit the area in the future.

Guest favorite

A cozy wooden space features two circular hanging chairs alongside a small table. A large, furry figure stands casually next to the chairs, showcasing the relaxed atmosphere. The warm wooden walls and floor contribute to the inviting interior design.

Place to stay in Wolfville

4.92 out of 5 average rating, 12 reviews

Sunken Escapes ZEEK (Unit 6)

DanielleRating, 5 stars3 weeks ago

We were greeted within minutes of arriving as there was a small glitch with the heat pump, which he was fixing. Everything was explained regarding the issue and the solutions to have it fixed right away. We rented #6, which gave plenty of privacy but yet still gave us a water view. The floor to ceiling windows were a great touch to help feel like you outside even when you were inside escaping the mosquitos and black flies. We both enjoyed kayaking on the lake as the sun was out in full summer heat. This is going to be our new favorite home when visiting our family. ❤️

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Vacation rentals in Middleton

Top-rated vacation rentals in Middleton

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