Vacation rentals in Middleton

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Top-rated vacation rentals in Middleton

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Guest favorite

Tiny home in Middleton

4.95 out of 5 average rating, 22 reviews

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

NS Registration # RYA-2023-24-03271619552440254-12468 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.

Aug 12 – 19

G$15,741 GYD per night

Guest favorite

Guest suite in Middleton

4.97 out of 5 average rating, 118 reviews

Cozy 3 Bedroom Annapolis Valley Hideaway

Experience comfort and relaxation in our spacious three-bedroom suite, nestled in the heart of the Annapolis Valley. Located in a quiet rural area, our renovated century farmhouse offers a peaceful retreat for your stay, and is an ideal base for exploring the beauty of Nova Scotia. Located within 5 minutes of Middleton, and within 20 minutes of Greenwood, Margaretsville, Cottage Cove, Lawrencetown, and Bridgetown. Annapolis Royal, Digby, Kejimkujik, Kentville, and Wolfville are within an hour.

Jan 14 – 21

G$19,631 GYD per night

Guest favorite

Home in Digby

5.0 out of 5 average rating, 129 reviews

The Beach House

No cleaning fees. The Beach House is about 15 minutes from of Digby & Digby Pines Golf Course. It is the perfect base for your whale watching trip. Explore Annapolis Royal, Kejimkujik, Bear River & Digby Neck, but make sure you leave time to relax on the deck & watch the fishing boats, maybe even whales & dolphin. Comb our rocky, cobblestone shoreline for sea glass or a special rock. Swim our cold, clear water if you dare! Digby is a fishing port so there is always lots to see there too.

Jun 18 – 25

G$35,780 GYD per night

Guest favorite

Cottage in Morden

4.97 out of 5 average rating, 150 reviews

Cozy Cottage in Quaint Village with Coastal Views

Steps from the Bay, tucked down a private lane in the quaint village of Morden, this cozy 1 bed cottage is the perfect coastal retreat. Newly renovated, it has everything you'll need for your stay. Sit by the wood burning stove and enjoy views of the nearby cliffs, or sunset views of the Bay from the dining area. Small but full kitchen, and a brand new four piece bath, including a soaker tub and outdoor shower off the bedroom. Private yard with outdoor seating to enjoy views. @grovecottage_ns

Jun 16 – 23

G$19,818 GYD per night

Guest favorite

Cottage in Middleton

5.0 out of 5 average rating, 26 reviews

Cozy 2 Bedroom Lakefront Cottage- Trout Lake

This charming & cozy cottage is located on beautiful Trout Lake, 15 minutes outside Middleton. It features 2 bedrooms, with additional sleeping on the double pull out sofa. Your comfort is ensured with a heat pump as well as an efficient fireplace. The open concept living area features a wall of windows allowing you to enjoy panoramic views of the lake and opens onto a spacious deck incl BBQ. Included in the rental is access to 4 kayaks so you can explore the lake from your private wharf.

Mar 11 – 18

G$30,817 GYD per night

Guest favorite

Tiny home in Saint John

4.99 out of 5 average rating, 133 reviews

Private Tiny House in the Woods

Ever wondered what it would be like to live in a tiny house? Well, this custom designed, 8'×28', high end tiny house on wheels is your opportunity! Experience tiny house living in a private, wooded setting. Fall asleep to the sound of the babbling brook, enjoy a BBQ, camp fire, or cozy up by the tiny wood stove. This is your place to relax and reconnect. There are trails through the woods to explore and a hanging cocoon tent to enjoy beside the brook. Less than 15 minutes from all amenities.

Sep 2 – 9

G$23,610 GYD per night

Guest favorite

Home in Crousetown

4.98 out of 5 average rating, 501 reviews

Cozy Riverside Cottage Indoor & Outdoor Fireplace

River music awaits. Escape the hustle and bustle of city life to embrace tranquility of nature nestled in a tiny home on 2 acres along a picturesque river. Stroll along the paths and unwind or cozy up by the fire with a good book. All this awaits you at Herons Rest. This is not just a home; it's a lifestyle! If you feel like venturing out, enjoy the beauty and fun offered by the South Shore, explore its abundant beaches, restaurants, shopping and music there is something for everyone!

Jan 7 – 14

G$22,487 GYD per night

Guest favorite

Cottage in Cottage Cove

4.96 out of 5 average rating, 166 reviews

Oceanfront Cottage w Sunset Views

Renovated top to bottom in 2019, this stylish cottage is nestled in perfect privacy by the trees with spectacular views of the Bay of Fundy! Start the day with local sourced coffee and teas, in a well-appointed kitchen. Spend your time exploring the shore via private beach access, or watching seals at the nearby park at low tide. Spectacular sunsets are sure to impress, especially from the look-off on the ledge! After the sun goes down, enjoy a fire roasting marshmallows under the stars.

Feb 4 – 11

G$42,096 GYD per night

Guest favorite

Tower in Broad Cove

4.99 out of 5 average rating, 199 reviews

Shackup Tower - 30 ft in the air & hot tub

Perched high on an ocean hillside, built on 30 ft tall steel legs, the cozy quarters above are akin to an old ship’s cabin. With 360 views at 30ft up you can chart the sun and stars across the sky, set your rhythm to the ebb & flow of the tide and scout the surf from above. Greet the evenings with a cozy woodstove, sunset with drinks on the deck, moonrise with a dip in the hottub & mornings with fresh espresso. Permit yourself to depart land for a while and come stand watch at The Tower.

Nov 15 – 22

G$121,522 GYD per night

Guest favorite

Home in Aylesford

4.98 out of 5 average rating, 162 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.

Sep 28 – Oct 5

G$19,419 GYD per night

Guest favorite

Guesthouse in Kingston

4.98 out of 5 average rating, 56 reviews

Whispering Oaks Studio

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 - and should you want to visit the south shore - Lunenberg is at the end of a scenic 75 min drive.

Oct 17 – 24

G$14,467 GYD per night

Guest favorite

Apartment in Berwick

4.94 out of 5 average rating, 139 reviews

Wildwood

Berwick is a funky town in the heart of the beautiful Annapolis Valley - an ideal location to explore orchards, vineyards, tides, farm markets and charming towns. Our bright, spacious and tastefully decorated flat is on our lovely country acreage, with gardens and private wooded trails. You are in a quiet, rural retreat yet only 3 minutes from town with groovy restaurants, boutiques, coffee shops and all amenities. This is one of the most vibrant areas of the Valley!

Sep 12 – 19

G$24,795 GYD per night