Chester Islands, Nova Scotia Vacation Rentals. Book Beach Rentals, Lake Houses, Condos, Cabins, Villas, and Homes in Chester Islands, Nova Scotia on RentalSaver.com!

Chester Islands Rentals

From $327 per night (USD)
VRBO
Attention Curse of Oak Island fans!
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Oak Island House is a newly restored and renovated century house which overlooks the famous Oak Island and the marina of ...
From $327 per night (USD)
VRBO
From $327 per night (USD)
VRBO
Cooperage Cottage - Peaceful & Family Friendly, Oceanfront
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Our quiet oceanfront Cooperage Cottage sits sheltered by tall oak, pine and spruce trees on five private acres of forest ...
From $327 per night (USD)
VRBO
From $437 per night (USD)
VRBO
Custom Built Home On The Scenic Waterfront Facing The Picturesque MarriottsCove
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
The main floor features a comfortably furnished, open concept Great Room, with sitting, kitchen and dining areas, as wel ...
From $437 per night (USD)
VRBO
From $164 per night (USD)
VRBO
Seascape,Art Deco cottage
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Two bedroom Art Deco cottage on 6 acre estate. Minutes from ocean and downtown amenities in the village of Chester. Ther ...
From $164 per night (USD)
VRBO
From $482 per night (USD)
VRBO
Gorgeous Oceanfront Estate with Heated Seawater Pool
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
This stylish Chester Cape Cod is now available for rent! Imagine vacationing by the sea, lying around your own pool enjo ...
From $482 per night (USD)
VRBO
From $442 per night (USD)
Expedia
Family Home In the Heart of the Village of Chester
Bedrooms:
4
Bathrooms:
5
Sleeps:
14
Spacious & Cozy Family Home in the Village of Chester 5 bedrooms, 2 & 1/2 baths, sleep’s 10 -14 adults and more Welcome ...
From $442 per night (USD)
Expedia
From $309 per night (USD)
VRBO
4 Bed (Sleeps 8) persons Vacation Rental with cottage, private dock and beach.
Bedrooms:
1
Bathrooms:
4
Sleeps:
8
Custom built, architect-designed, open concept house and separate country-style cottage, Swallow Point Retreat sits high ...
From $309 per night (USD)
VRBO
From $133 per night (USD)
Expedia
A Sailor's Paradise - Stevens Cove Guest Quarters
Bedrooms:
1
Bathrooms:
1
Sleeps:
2
Just steps from the wharf you'll find Stevens Cove Guest Quarters. The apartment is at ground level with a spacious deck ...
From $133 per night (USD)
Expedia
From $200 per night (USD)
VRBO
Seaside Cottage - Blandford, Nova Scotia, Canada
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
LOCATED 15 MINUTES FROM CHESTER, NOVA SCOTIA The Cottage is a century home, with an unparralled view of the cove in the ...
From $200 per night (USD)
VRBO
From $320 per night (USD)
VRBO
Stoneybrook House - historic property on 1.7 acres of land
Bedrooms:
2
Bathrooms:
6
Sleeps:
12
Welcome to Stoney Brook House, 150 years old in 2010. This historic landmark is located just across Highway Three from t ...
From $320 per night (USD)
VRBO
From $699 per night (USD)
VRBO
Breathtaking Oceanfront Chateau
Bedrooms:
3
Bathrooms:
4
Sleeps:
10
Tranquility awaits at “Harbour Mist” on the Aspotogan Peninsula with 192 feet of private oceanfront. This stunning stone ...
From $699 per night (USD)
VRBO
From $104 per night (USD)
Expedia
Oceanfront cozy comfortable cottage!
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
If you like having access to a large front deck/porch with a fabulous waterview, it’s own private beach then this is the ...
From $104 per night (USD)
Expedia
From $613 per night (USD)
VRBO
Superb Oceanfront with Optional Boathouse
Bedrooms:
2
Bathrooms:
4
Sleeps:
10
This outstanding multi-faceted oceanfront property in Otter Point has privacy without isolation, panoramic western sunse ...
From $613 per night (USD)
VRBO
From $317 per night (USD)
VRBO
Ahoy!...Oceanfront Family Cottage with Hot Tub, Near South Shore Attractions
Bedrooms:
1
Bathrooms:
3
Sleeps:
7
Come and Relax at this private family cottage with direct waterfrontage and floating dock. This Nova Scotia cottage rent ...
From $317 per night (USD)
VRBO
From $276 per night (USD)
VRBO
Spectacular Ocean Sunset Views
Bedrooms:
2
Bathrooms:
4
Sleeps:
7
This century-old fisherman's home has been lovingly restored, and features four bedrooms, two living rooms, a modern, we ...
From $276 per night (USD)
VRBO
From $182 per night (USD)
Expedia
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
Unique cove beach surrounding, beautiful, tranquil, and private, this water front house is in the famous beach town Ches ...
From $182 per night (USD)
Expedia
From $171 per night (USD)
VRBO
The Captain’s Quarters 2 bedroom harbourview condo
Bedrooms:
1
Bathrooms:
2
Sleeps:
5
Located in the heart of sea-side Chester, Nova Scotia with a gorgeous, full view of the front harbour. The Captain’s Qua ...
From $171 per night (USD)
VRBO
$Oceanfront Luxury Magical Views Sunset and Sunrise\n$
From $244 per night (USD)
Expedia
Oceanfront Luxury Magical Views Sunset and Sunrise\n
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Luxurious 3 level townhouse with high end furnishings, art work, Persian carpets throughout. Located at The well known ...
From $244 per night (USD)
Expedia
From $356 per night (USD)
VRBO
The oceanside Hideaway is nestled between the trees with stunning ocean views
Bedrooms:
3
Bathrooms:
2
Sleeps:
6
Looking to relax in a stunning oceanside house with close proximity to Halifax NS? The Hideaway is your spot, just 30 mi ...
From $356 per night (USD)
VRBO
$Luxury Accomodation, Footsteps from the Ocean.\n$
Click For Pricing
Expedia
Luxury Accomodation, Footsteps from the Ocean.\n
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to The Crow’s Nest. A Luxurious vacation destination in Chester. A three bedroom home; Centrally located in th ...
Click For Pricing
Expedia
From $257 per night (USD)
VRBO
Relax on the South Shore, steps from 2 beaches, ocean views & hot tub.
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
On the Aspotogan peninsula in the quiet community of East River, this beautiful renovated three bedroom two bathroom ...
From $257 per night (USD)
VRBO
From $410 per night (USD)
Expedia
Large, modern Cape Cod style cottage in oceanside charming town
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Sweeping ocean views, across the road from the beach, looking out over yacht club and sailboats - steps to the restauran ...
From $410 per night (USD)
Expedia
From $193 per night (USD)
VRBO
Cozy Oceanfront Escape with Hot Tub
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
High above the ocean, this contemporary two-bedroom cottage provides sweeping coastal views, stunning sunsets, and a can ...
From $193 per night (USD)
VRBO
From $221 per night (USD)
Expedia
Peaceful 2-Bedroom Coastal Cottage with Hot Tub
Bedrooms:
1
Bathrooms:
2
Sleeps:
4
High above the ocean, this contemporary two-bedroom cottage provides sweeping coastal views, stunning sunsets, and a can ...
From $221 per night (USD)
Expedia
From $526 per night (USD)
VRBO
The Chester House, oceanside in the village, private wharf
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
An acre on the ocean in Chester's front harbour, this historic gem was once a Lobster Plant dormitory and has been lovin ...
From $526 per night (USD)
VRBO
From $528 per night (USD)
VRBO
The Oaks Seaside Retreat
Bedrooms:
5
Bathrooms:
5
Sleeps:
10
The Oaks Seaside Retreat has been a historic inn, elegant personal residence and now after an architecturally inspired ...
From $528 per night (USD)
VRBO
From $712 per night (USD)
VRBO
White Cottage, An East Coast Architectural Masterpiece
Bedrooms:
6
Bathrooms:
4
Sleeps:
8
NEW for 2025 - White Cottage, synonymous with endless charm, true grace and elegant oceanfront living since 1795. One of ...
From $712 per night (USD)
VRBO
From $441 per night (USD)
VRBO
In ground HOT TUB + 2 primary bedrooms w/ ensuites
Bedrooms:
2
Bathrooms:
2
Sleeps:
4
Enjoy a four-season swim spa at our serene retreat on the scenic Aspotogan Peninsula, just 4 minutes from Bayswater Beac ...
From $441 per night (USD)
VRBO
From $643 per night (USD)
VRBO
Witmere - True Vacation Elegance
Bedrooms:
3
Bathrooms:
4
Sleeps:
8
Witmere - true vacation elegance. Exuding sophistication & refinement, characterized by clean lines, the highest-qualit ...
From $643 per night (USD)
VRBO
From $715 per night (USD)
Expedia
Spacious Exclusive 5-bedroom house in fabulous Chester with WiFi, AC
Bedrooms:
4
Bathrooms:
5
Sleeps:
10
Get ready to relax in this 5-bedroom house in Chester. With 2 king beds, 1 queen bed, 1 full bed, and 2 twin beds, this ...
From $715 per night (USD)
Expedia
From $581 per night (USD)
VRBO
Charming 3-bedroom exclusive house with WiFi, AC in serene Chester
Bedrooms:
3
Bathrooms:
3
Sleeps:
6
Chester is waiting for you at this 3-bedroom house. Nestled in a peaceful neighbourhood, this fabulous retreat offers 1 ...
From $581 per night (USD)
VRBO
From $285 per night (USD)
Expedia
One 12 Queen
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
This one-of-a-kind property boasts a unique style and beautiful water views, all located in the heart of Chester. From t ...
From $285 per night (USD)
Expedia
From $212 per night (USD)
VRBO
Quaint home conveniently located between Chester and Mahone Bay.
Bedrooms:
1
Bathrooms:
3
Sleeps:
6
Rest in the quiet peace of Chester Basin, just steps from the beautiful coast walk down Borgalds Point road. Convenientl ...
From $212 per night (USD)
VRBO
From $94 per night (USD)
VRBO
Conveniently located in the centre of the South Shore. Close to everything
Bedrooms:
0
Bathrooms:
3
Sleeps:
2
Nestled in the quaint village of Chester Basin, this adorable little bunkie offers a blend of comfort ( electricity, wif ...
From $94 per night (USD)
VRBO
From $260 per night (USD)
VRBO
Authentic South Shore Farm House
Bedrooms:
2
Bathrooms:
4
Sleeps:
8
Steps from famed Oak Island sits a true treasure of the South Shore. All the character of an original farm house (circa ...
From $260 per night (USD)
VRBO
From $855 per night (USD)
VRBO
Back Harbour House - Remarkable Chester Waterfront
Bedrooms:
3
Bathrooms:
2
Sleeps:
4
New for 2025 ... Not 'near' the water, not even 'on' the water, but 'IN' the water! One of the most unique stays on th ...
From $855 per night (USD)
VRBO
From $247 per night (USD)
VRBO
Chester Village Charmer
Bedrooms:
2
Bathrooms:
3
Sleeps:
5
Welcome to Tamarack, a charming century home in the heart of Chester Village. The house is a short walk to the Chester Y ...
From $247 per night (USD)
VRBO
From $444 per night (USD)
VRBO
Chester Village Gem – Elegant Coastal Retreat Sleeps 6
Bedrooms:
2
Bathrooms:
3
Sleeps:
6
Welcome to your perfect seaside escape in the heart of Chester, Nova Scotia. This newly renovated, beautifully appointed ...
From $444 per night (USD)
VRBO
From $184 per night (USD)
VRBO
Cozy cottage by the river perfect for nature lovers & pet friendly
Bedrooms:
1
Bathrooms:
3
Sleeps:
4
Escape the hustle and bustle and immerse yourself in the tranquility of nature at our charming cottage by the river. Nes ...
From $184 per night (USD)
VRBO
From $124 per night (USD)
VRBO
ChesterVillage · Charming Chester Classic in Village Core
Bedrooms:
2
Bathrooms:
3
Sleeps:
7
Charming 3-Bedroom Classic Home in the Heart of Chester. Escape to this delightful two-story home, designed to offer a p ...
From $124 per night (USD)
VRBO

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Chester Islands Rentals

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Results: 40 Rentals