
Cottage holiday rentals in Chester
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Nightly prices starting at
Chester holiday rentals start at $204 SGD per night before taxes and fees

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

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

The Shore Shack
Shore Shack is a newly construction timber frame cabin on the Atlantic Ocean. Beautiful views and direct oceanfront. A Sandy beach within walking distance (at the end of Sand Beach road). The town of Liverpool is a five minute drive away. Very private! Whitepoint, Carter's and Summerville beach all a short drive away. A four person hot tub was added in March 2022. This property does not have an oven - does have 4 burner stove. Nova Scotia Tourist Registry RYA-2023-24-04142056359520676-77

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.

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.

A Secluded Lakefront Spectacle
Kick back and relax in this calm, stylish space. This lake side cottage is located minutes from the historic towns of Lunenburg and Mahone Bay. Regardless of which direction you go, there is an abundance of choices. Whether you enjoy outdoor activities such as beaches, hiking, off road and water sports, or would rather site see and dine out, this area offers it all. If relaxing while overlooking the lake is what you would prefer then this is the perfect setting.

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 cottage rentals in Chester
Cottage rentals with a hot tub

Nova Scotia A-Frame with Hot Tub

SeaMist Cottage - Summerville Centre, NS

Birchwood on the Lake (with Hot Tub)

Oceanside Home within the City; A Cycle Away!

Waterfront Cottage on Lake with Hot Tub + Rec Room

Herring Hole Hideaway

Relaxing Oceanfront Retreat- private luxury

Wildberry Cottage
Pet-friendly cottage rentals

Waterfront cottage, private beach, LaHave River.

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

Seawind Cottage

Serene Cottage on 10 acres, Hot Tub, Lake Access

“Tranquility Cove” a Private Waterfront Oasis

Lakeview Cottage on Zwickers Lake

Conrad Beach Cottage

Seaside Designer Destination - Mosher's Cottage
Private cottage rentals

Cove Cottage | Second Peninsula

Cheerful/ fun three bedroom lake house

Southshore Ocean Beach Cottage

Tranquil Lakefront Retreat with Private Sauna

Sunset Cove Cottage Kayak+Paddleboard+ Paddleboat

Rose Cottage - Walking Distance to 2 Beaches

Gopher Lodge (Family and couples oriented getaway)

Lakefront Cottage~Pets4Free~Private Beach~BBQ~View
Destinations to explore
- Halifax Holiday rentals
- Bar Harbor Holiday rentals
- Mid-Coast, Maine Holiday rentals
- Moncton Holiday rentals
- Cape Breton Island Holiday rentals
- China Holiday rentals
- Charlottetown Holiday rentals
- Lunenburg County Holiday rentals
- Fredericton Holiday rentals
- Saint John Holiday rentals
- Dartmouth Holiday rentals
- Kennebec River Holiday rentals
- Rentals with outdoor seating Chester
- House rentals Chester
- Family-friendly rentals Chester
- Rentals with a washing machine and dryer Chester
- Rentals with a patio Chester
- Pet-friendly rentals Chester
- Cabin rentals Chester
- Rentals with beach access Chester
- Rentals with a fireplace Chester
- Cottage rentals Nova Scotia
- Cottage rentals Canada
- Oak Island
- Rissers Beach Provincial Park
- Hirtle's Beach
- Halifax Citadel National Historic Site
- Rainbow Haven Beach
- Lawrencetown Beach Provincial Park
- Conrad's Beach
- Point Pleasant Park
- Canadian Museum of Immigration at Pier 21
- Halifax Public Gardens
- Halifax Waterfront Boardwalk
- Dalhousie University
- Maritime Museum of the Atlantic
- Long Lake Provincial Park
- Halifax Central Library
- Kejimkujik National Park & National Historic Site
- Luckett Vineyards
- Shubie Park
- Big Mushamush Lake
- Peggys Cove Lighthouse
- Halifax Seaport Farmers' Market
- Grand-Pré National Historic Site
- Ski Martock
- Bayswater Beach Provincial Park





