
Cottage vacation rentals in Chester
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Top-rated cottage rentals in Chester
Guests agree: these cottages are highly rated for location, cleanliness, and more.

Serene Cottage on 10 acres, Hot Tub, Lake Access
GREENWOOD COTTAGE - 10min drive from Chester. Nestled on 10 acres of private forest, Greenwood Cottage awaits. If you seek an escape from the city, this 3 king sized bedrooms, on one level - 20ft vaulted ceilings in the Main living area. It is perfect for families, friends and couples. After a long day exploring, hiking or visiting Chester. The Hot Tub will be welcomed or cozy on up to the woodstove with your loved ones. Sensea Spa , Chester, Lunenburg and Mahone Bay are a short drive away

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

Kaikoura Cottage - In the Heart of Mahone Bay
Kaikoura Cottage in the heart of the iconic town of Mahone Bay is a newly (2021) renovated 2 bedroom, 2.5 bath tastefully appointed cottage a short stroll to the picturesque waterfront or the popular multi use rails to trails. This peaceful space is at the epicenter of so many potential adventures. Kayak along the coast, visit the beach, stroll the historic town of Lunenburg, bike the trail, enjoy the local brew pub, relax at Chester's Sensea Nordic Spa. It's all yours to savour and enjoy.

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

Wilson's Coastal Club - C5
Beautiful oceanfront 1-bedroom cottage with a King bed. Enjoy the deck with a propane BBQ, patio furniture, and stunning views of St. Margaret's Bay. The bathroom features a 2-person jet tub and separate shower. Free high-speed Wi-Fi and Internet TV included. Additionally, guests can add on our unique wood-fired hot tub experience for an extra fee. See “Other things to Note” for details. Feel free to reach out with any pricing questions as Airbnb doesn't always show all available rates.

Spacious Lakefront Cottage Retreat
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.

The Old Kettle Cabin with Hot Tub
Get cozy and settle in to this inviting space with your significant other, or getaway by yourself for some sought after rest and relaxation. Nestled privately off the road, the cabin offers beautiful views of the Historic Medway River in a tranquil nature setting. Watch the tide come in and out from the large deck, or venture out into the many trails nearby on the electric bikes. This space encourages both adventure and relaxation, and will be sure to bring you and yours closer.

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.

Moss Cottage on the Lake
Moss Cottage can be your getaway only 45 minutes from Halifax and a few kilometers from the village of Chester on Nova Scotia's beautiful south shore. It's your choice to take in the many local sights, shop in towns and villages that dot the coastline, sail, play golf or stretch out on any number of beaches -- all within easy driving. Or, perhaps you'd prefer to stay put at Moss Cottage for a lovely chance at solitude and a dip in our crystal clear, spring fed lake.

The Beach Loft: 5-bedroom
This pretty beach house is located just steps from the beautiful Seawall beach. Relax in the hot tub, hammock or next to the fire. The perfect getaway that is only 34min from Halifax. Featuring a wood burning fireplace and stone accents. Private hot tub overlooking the ocean. Post and beam Construction. Ocean views. Seawall beach is between Queensland and Cleveland’s beach. Also located on Rails to Trails path. Minutes to restaurants and coffee shops in Hubbards.

Waterfront Retreat
If you are looking for a peaceful, country retreat on the water, you've found it! Welcome to our beautiful house on the Atlantic Ocean, only a 20 minute drive from the gorgeous, colourful towns of Chester and Hubbards, and approximately an hour away from Mahone Bay, the well-known town of Lunenburg, and the city of Halifax. The South Shore of Nova Scotia boasts plenty of shopping, restaurants, and summer activities that interact with the breathtaking scenery.

Peaceful 2-Bedroom Coastal Cottage with Hot Tub
High above the ocean, this contemporary two-bedroom cottage provides sweeping coastal views, stunning sunsets, and a canopy of starry skies. Overlooking the entrance to Deep Cove, and out towards Chester, Nova Scotia, this secluded four-season cottage offers an idyllic escape, ideal for a romantic couple's getaway or a tranquil retreat from the everyday.
Popular amenities for Chester cottage rentals
Cottage rentals with a hot tub

A Secluded Lakefront Spectacle

Birchwood on the Lake (with Hot Tub)

Oceanside Home within the City; A Cycle Away!

New Lakefront Luxury Cottage w/ Hot Tub

A Dream Cottage in a Village by the Sea

Herring Hole Hideaway

Wildberry Cottage

Sunset Cove - Private Hot Tub & Lake Access
Pet-friendly cottage rentals

Waterfront cottage, private beach, LaHave River.

"Lisette's on Long Hill", cozy with boho charm

Seawind Cottage

“Tranquility Cove” a Private Waterfront Oasis

Charming Historic Cottage on Main in Mahone Bay

5 Star Lakefront Cottage on Tranquil Hennigar Lake

Tide's Inn Lake House, Lake Torment,East Dalhousie

Viola’s House. Idyllic Oceanfront Cottage
Private cottage rentals

Cove Cottage | Second Peninsula

Idyllic Ocean Front Nova Scotia Cottage

River Breeze Cottage

Cheerful/ fun three bedroom lake house

Southshore Ocean Beach Cottage

Tranquil Lakefront Retreat with Private Sauna

Loon Song Retreat

Finnigan's Landing
Quick stats about cottage rentals in Chester

Nightly prices starting at
Chester vacation rentals start at G$33,469 GYD 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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- Rentals with a fireplace Chester
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- Pet-friendly rentals Chester
- Rentals with beach access Chester
- Family-friendly rentals Chester
- Rentals with a washer and dryer Chester
- Rentals with a patio Chester
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- Cottage rentals Nova Scotia
- Cottage rentals Canada
- Rissers Beach Provincial Park
- Oak Island
- Hirtle's Beach
- Halifax Citadel National Historic Site
- Rainbow Haven Beach
- Lawrencetown Beach Provincial Park
- Conrad's Beach
- Dalhousie University
- Halifax Waterfront Boardwalk
- Halifax Public Gardens
- Point Pleasant Park
- Canadian Museum of Immigration at Pier 21
- Maritime Museum of the Atlantic
- Long Lake Provincial Park
- Halifax Central Library
- Shubie Park
- Big Mushamush Lake
- Luckett Vineyards
- Halifax Seaport Farmers' Market
- Kejimkujik National Park & National Historic Site
- Peggys Cove Lighthouse
- Ski Martock
- Grand-Pré National Historic Site
- Chester Golf Club





