Chester Islands Rentals
From $442 per night (USD)VRBO
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)VRBO
From $309 per night (USD)Expedia
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)Expedia
From $133 per night (USD)VRBO
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)VRBO
From $581 per night (USD)Expedia
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)Expedia
From $285 per night (USD)VRBO
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)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 $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 $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 $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 $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 $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
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 $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 $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 $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
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
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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 ...
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From $257 per night (USD)Expedia
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)Expedia
From $410 per night (USD)VRBO
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)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 $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 $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 $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 $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 $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