Vacation rentals in Chester

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness, and more.

SUPERHOST
  1. Entire home
  2. Chester
The Whale House

The Whale House offers bright panoramic water views from every room. Centrally located in the beautiful Village of Chester steps away from marinas, eclectic restaurants, artisan shops, beach, and yacht club. Open concept with large deck to eat and enjoy the stunning views of boats sailing by. Well appointed and beautifully decorated with fireplace and comfy furniture. Three large bedrooms, 2 full baths, fully equipped chef style modern Ikea kitchen. A true place to harbour.

  1. Entire rental unit
  2. Marriotts Cove
Sailors’ Paradise - Stevens Cove Guest Quarters

Just steps from the wharf you'll find Stevens Cove Guest Quarters. The apartment is at ground level with a spacious deck overlooking the mooring field. The bay is dotted with boats in this very active sailing community of Chester - home to the largest keel-boat regatta in North America. Whether you are a sailor or just enjoy the water view this is the place to see boats large and small, modest and grand from May through October. The posted price includes 15% Harmonized Sales Tax.

  1. Entire cottage
  2. Chester
Spectacular 2 Bedroom Lake House!

Join us on Stanford Lake for your next getaway! This newly built home has a Scandinavian feel and overlooks a peaceful lake. Sprawl out on your king sized bed and take in the gorgeous views of Sensea Nordic Spa. Minutes from the Chester Yacht Club and Chester Golf Club. Chester Village, grocery stores, liquor store, bars and restaurants are all within walking distance. A short drive to many beautiful beaches, historic Lunenburg, Mahone Bay, Hubbards, and world famous Oak Island.

Vacation rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Other great vacation rentals in Chester

  1. Entire guest suite
  2. Chester
Chester studio, walk to Nordic Spa , Golf & More
  1. Entire home
  2. Chester
Charming century-old three bedroom home In Chester
  1. Entire home
  2. Chester
Original Chester Character ( Dutchess on Queen)
  1. Entire home
  2. Chester
The Crow’s Nest. Coastal, Modern, Perfect.
  1. Entire cottage
  2. Chester
The Barn (Chester Oceanfront)
SUPERHOST
  1. Entire home
  2. Chester
Charming Seaside Village Home
SUPERHOST
  1. Entire cottage
  2. Chester
Chester Basin Vacation Retreat Oceanfront
  1. Entire rental unit
  2. Chester
Central Chester Casa
  1. Entire cottage
  2. Chester
Squid Cove Cottage on ocean
SUPERHOST
  1. Entire cottage
  2. Chester
The Boathouse on Scotch Cove
SUPERHOST
  1. Entire condo
  2. Chester
The Captain's Quarters 2 bedroom harbourview condo
  1. Entire guest suite
  2. Chester
Chester Village Suite Steps from Ocean