Chester Rentals
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 $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 $69 per night (USD)VRBO
Serenity Tiny House Cottage in Chester
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
This brand new storybook 665 Sq. ft. Tiny House Cottage sits on a meticulously landscaped private 2 acres of gardens and ...
From $69 per night (USD)VRBO
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 $175 per night (USD)VRBO
Mid century modern home for rent in sought after Chester
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This sweet mid century modern home is just minutes from the village of Chester. Only minutes walk to the village of Ches ...
From $175 per night (USD)VRBO
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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 $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 $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 $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 $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 $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 $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