Cottage holiday rentals in Chester

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Top-rated cottage rentals in Chester

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Top guest favourite
A spacious deck overlooks the tranquil LaHave River, featuring a dining table accompanied by six chairs and two lounge chairs positioned for relaxation. A large umbrella provides shade, enhancing the outdoor seating area with natural views of the water and surrounding greenery.
Cottage in LaHave
4.99 out of 5 average rating, 102 reviews

Waterfront cottage, private beach, LaHave River.

Stone’s Throw Cottage, century old, recently modernized, 550 sq. ft. inside, 400 sq. ft. deck, on the LaHave River and it’s own oceanfront, private pebble beach. Located on quiet Pentz Road, on the beautiful South Shore. Two minutes from famous LaHave Bakery, enjoy a morning coffee, a harty lunch or fresh baked treat. Nearby historic LaHave ferry for a 20 minute drive to Lunenburg, a UNESCO World Heritage Site. 15 minutes to Nova Scotia’s best white sand beaches, Risser’s, Crescent, & Green Bay.

Top guest favourite
A serene lakefront view captures the luxury lake house surrounded by trees. The structure reflects gently in the calm water, showcasing warm tones from the setting sun. A private beach area with sand and a dock is visible, enhancing the tranquil atmosphere.
Cottage in Hubbards
4.98 out of 5 average rating, 255 reviews

Fox Point Lake House - Luxury Lakefront Rental!

Featured on Home Shores - Season 2, Episode 1! This one of a kind luxury lake house has plenty to offer. Gorgeous lakefront, private beach, hot tub that overlooks the lake, water views from the main floor and primary bedroom, wood fireplace and the list goes on. Other features include: - 30 mins from Halifax - Cathedral ceilings with A frame front - Built in wet bar with wine and beer fridge - Private sand beach - Salt water hot tub that comfortably sits 7 Check our IG - @foxpointlakehouse

Top guest favourite
The cabin's entrance features a spacious wooden deck with stairs, surrounded by greenery. A propane grill is positioned next to bright orange and red Adirondack chairs, inviting relaxation. The exterior is constructed of wood, combining natural tones with large windows for ample light.
Cottage in Windsor
4.92 out of 5 average rating, 352 reviews

Knotty Pine Cottage - cozy lakeside getaway!

Welcome to Knotty Pine Cottage - the perfect place to relax and enjoy nature. This 2-bedroom, 1 bathroom cottage has everything you need for your year-round getaway. Located in beautiful Chalet Hamlet, a private quiet cottage community that offers a relaxing retreat from the busy pace of everyday life. Beautiful Armstrong Lake is across the road, as is the community swimming area and boat launch. Knotty Pine Cottage is located 10 minutes from Martock/OnTree, and 20 minutes from Windsor.

Superhost
An open-concept living area showcases a blend of rustic and modern design elements. A wood stove stands beside a large window, allowing natural light to fill the space. Two chairs and a small table create a cozy nook, complemented by sleek cabinetry and polished wooden floors.
Cottage in Martins Point
4.94 out of 5 average rating, 211 reviews

OTW Close 2 Nordic Spa — Accepting Travel Nurses

• "Occupancy Fees or Property use tax" are local sales taxes charged by Airbnb (HST 15%) • 3pm Checkin • 15 mins to NORDIC Spa • 10 mins from Mahone Bay & Oak Island • Free bikes with access to the Chester Connection Trail • BBQ, full kitchen and utensils, A/C, cable TV, wifi and parking • Open-concept living • Full bath on the main floor, 2 bedrooms on the second floor • The house is 100 years old so the stairs are steep • Porch has shared laundry facilities for the guesthouse next door

Guest favourite
A rustic log cottage is shown with a wooden deck leading to a light-colored door. A fenced area is visible beside the entrance, with a gravel driveway extending in front. Green grass is seen in the background, bordered by trees.
Cottage in Lunenburg
4.92 out of 5 average rating, 253 reviews

Wildwood Acres

Welcome to Wildwood Acres! This peaceful log cottage is located on Second Peninsula, just 6 minutes from the vibrant town of Lunenburg. With almost 3 acres and a fenced in area, your dog will be able to enjoy this spot as much as you will. Whether the occassion is a family vacation, or relaxing weekend away with your friends, this Wildwood Acres is just what you need! There are many options for dining and activities in Mahone Bay or Lunenburg, and Bachman's beach is just down the road.

Guest favourite
The modern kitchen features stainless steel appliances, including a refrigerator and stove. White cabinetry contrasts with a warm orange accent wall. A window allows natural light, highlighting the spacious layout and functional countertop space, with a decorative rug positioned on the dark wood floor.
Cottage in Hubbards
4.82 out of 5 average rating, 149 reviews

Emily's Seaside Escape

Beautiful cottage overlooking St. Margarets Bay. This 2 bedroom 1 bathroom cottage sleeps 4. Less than 1 hour to downtown Halifax NS. Wood burning stove, fridge, stove, dishwasher, microwave and washer and dryer. Peggy's Cove and the beautiful Chester/Mahone Bay shoreline are all an easy drive away. The quaint village of Hubbards is a mere 10 minute drive as are sand beaches in either direction. Relax and surround yourself with the calming ocean views of Emily's Seaside Escape.

Top guest favourite
A welcoming porch is adorned with two light blue adirondack chairs, positioned to overlook a serene lake. The ground is covered in vibrant autumn leaves, and trees in the background are reflected in the calm water. The scene captures a peaceful outdoor retreat.
Cottage in Chester
4.96 out of 5 average rating, 173 reviews

Large Pet Friendly Lakefront cottage in Chester

This pet friendly, four season cottage is the perfect space to escape the city with a loved one for a weekend or for your next family vacation! Only 50 minutes from Halifax, it’s in perfect proximity between downtown Chester and Windsor. The home Includes a large eat in kitchen with sitting area, bathroom, laundry and two bedrooms on the main level and a walkout primary bedroom and large living room with wood stove on the lower level and a large walk out deck overlooking the lake.

Top guest favourite
A charming boathouse is positioned on a wooden dock, surrounded by lush greenery. The elevated deck features a glass railing, offering unobstructed views of the water. Two wooden benches provide seating, inviting relaxation in the serene seaside setting.
Cottage in Chester
4.95 out of 5 average rating, 109 reviews

The Boathouse on Scotch Cove

This little boathouse sits right on Scotch Cove in East Chester, NS. Enjoy seaside views from every angle, with lovely outdoor seating and propane BBQ. The deck leads directly to the dock allowing for easy access for swimming or watercraft provided. The place is just a short walk from hiking and biking trails, with nearby lakes and sandy beaches. The indoor projector and screen make movie nights so much better! The boathouse is fully equipped for winter with a cozy woodstove.

Top guest favourite
A bright kitchen space is highlighted by large windows that offer ocean views. The area features a light wood island with seating, a minimalist design complete with white cabinetry, and decorative items arranged on a nearby shelf. Natural light enhances the clean, airy atmosphere.
Cottage in Rose Bay
4.97 out of 5 average rating, 115 reviews

South Shore cottage with ocean views

▪ Located in the South Shore, only 20 minutes to Lunenburg ▪ Character home renovated for modern and relaxed comfort ▪ 1,200 sq/ft of bright living space ▪ Expansive and tranquil ocean views of Rose Bay ▪ Intimate soaker tub and dreamy bathroom ▪ Outdoor living space with BBQ and fire pit ▪ Inspired by the picturesque, seaside villages of Kingsburg and Lunenburg ▪ Only minutes from Gaff Point and Hirtle's Beach ▪ Unwind in the wood-burning hot tub (closed during the Winter)

Top guest favourite
The exterior of the cottage features a spacious deck with red chairs inviting relaxation. Surrounding greenery includes mature trees and landscaped grass, creating a serene outdoor space. The cottage itself has a welcoming facade with multiple windows and a chimney, situated in a natural setting.
Cottage in Boutiliers Point
4.98 out of 5 average rating, 115 reviews

Palmer Cottage

Quiet. Cozy. Quaint. Everything you need for a relaxing visit to the South Shore of Nova Scotia. Nestled in between Halifax and Chester, Palmer Cottage is uniquely situated to take advantage of numerous local attractions - all within a short drive. Several beaches are located within minutes of Palmer Cottage, including Queensland Beach, Cleveland Beach and our very own Cowlow Cove beach - only a minute's walk from the cottage! Local amenities are only 10 minutes away!

Top guest favourite
A quaint exterior view of Burns Cove Cottage features colorful adirondack chairs in vibrant blue and green. Flower-filled baskets adorn the windows, contributing to the inviting appearance. A stone pathway bordered by grass leads to the entrance, enhancing the cottage's charm.
Cottage in Lunenburg
4.99 out of 5 average rating, 110 reviews

Burns Cove Cottage. Superb home, fabulous views.

Burns Cove cottage is a spacious, fully equipped vacation home. The waterfront location makes it a prime spot to relax, view nature. It’s also a great location to bike/ hike/drive the Lighthouse Route and Rails to Trails. Lunenburg, Mahone Bay, Chester and Bridgewater have some amazing local eateries, craft breweries, local wineries and lots of shops. A quick drive to the free ferry ride gets you to the LaHave bakery, crafts, pottery, art galleries and many beaches.

Top guest favourite
A wood-fired hot tub sits beside a serene oceanfront, surrounded by wooden decking and trees. Sunlight reflects off the open water, creating a peaceful atmosphere. A chimney rises from the tub, indicating its warm, inviting nature.
Cottage in Boutiliers Point
4.98 out of 5 average rating, 125 reviews

Wilson's Coastal Club - C6

Cozy oceanfront studio cottage with queen bed made for romantic escapes or solo resets. Features a covered deck with propane BBQ, propane fireplace, fully equipped kitchen, Smart TV, and access to a guests-only private beach. Pet friendly, peaceful, and just 30 minutes from Halifax. Optional add-on for the woodfired saltwater hot tub and seaside sauna. See “Other things to Note” for details on our woodfired amenities. Feel free to reach out with any pricing questions.

Popular amenities for cottage rentals in Chester

Quick stats about cottage rentals in Chester

  • Nightly prices starting at

    Chester holiday rentals start at $206 SGD per night before taxes and fees

  • Verified guest reviews

    Over 230 verified reviews to help you choose

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Chester rentals

  • 4.9 Average rating

    Chester stays are highly rated by guests – averaging 4.9 out of 5!

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