Skip to content
Sign up
Log in
Vacation rentals in Chester

Vacation rentals in Chester

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Chester

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

  • Cozy Cottage on South Shore. 30 min from Halifax!
    SUPERHOSTEntire cottage · 2 guests · 1 bed · 1 bathroom
    Cozy Cottage on South Shore. 30 min from Halifax!

    A very cozy and peaceful place to base any vacation on the South Shore out of. Very close to hiking and ATV trails. No visible neighbors from the yard, lots of wildlife. Large parking areas. Interior is a mixture of new and re purposed materials. Appliances are small but functional, all the comforts of home but smaller. Double bed is incredibly comfortable. The building is compact but well laid out for function. It's my favorite place to be.

    What guests are saying:

    “If you are looking for a peaceful retreat this is your place! Michelle's little cottage is private and quiet. We had our dogs there and they had lots of space to run and play. Her location its perfectly located to chester and mahone bay for little day trips. We were there in the spring but I can imagine it would be a perfect spot for a summer trip!”

  • Moss Cottage
    SUPERHOSTEntire cabin · 2 guests · 1 bed · 1 bathroom
    Moss Cottage

    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 lake.

    What guests are saying:

    “What a beautiful place Moss Cottage was! From the moment we walked down the stone stairway to the front door my fiance and I were entranced by the magic this place holds. There was always something to do here, and whether we were playing board games or watching a large selection of DVDs next to a cozy wood stove we always felt like we were in our home away from home. The spectacular lake view never disappointed and was a dream to wake up to every morning, and with the fall leaves floating on the lake and peppering the lawn the view was like a painting I couldn't take my eyes off of. We even got out on the boat a couple times and the lake looked just as amazing from the boats perspective. I'm sure I'm forgetting a lot of things but all in all the hospitality and small touches that Cindy and Moss Cottage provide make this place feel like your own. I would absolutely recommend this place to my family and friends and I will absolutely be back again. Thank you infinitely, Justin”

  • A great South Shore location for your Staycation!
    SUPERHOSTEntire guest suite · 2 guests · 1 bed · 1 bathroom
    A great South Shore location for your Staycation!

    We have the perfect package for your Lunenburg County Staycation. Just 3 minutes from Mahone Bay and 7 from Lunenburg, our suite gives you everything you need. A real home from home experience with the convenience of a full kitchen, relaxing living room, spacious bedroom and bathroom! A welcoming property exploding with greenery! Explore the shores, relax at one of the local beaches during the day and enjoy an evening by the fire pit with a glass of wine!

    What guests are saying:

    “If you are looking for a home base from which to explore the lovely south shore this might be for you. It is close to everything but on a quiet back road. The space is large, has everything a couple or single would need, delightful touches by the host (holiday decorations while we visited), and is quiet and private. Communication was quick and easy. All in all we had a wonderful stay.”

Holiday rentals for every style

Get the amount of space that is right for you.

  • Homes
  • Hotels
  • Unique stays

Popular amenities for Chester holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Chester

Pioneer Cottage 8km from Chester's New Sensea Spa
SUPERHOSTEntire guest house
Pioneer Cottage 8km from Chester's New Sensea Spa
Price:€71 / night
Squid Cove Cottage on ocean
SUPERHOSTEntire cottage
Squid Cove Cottage on ocean
Price:€127 / night
Oakland Suite - Mahone Bay Three Churches Vista
SUPERHOSTEntire guest suite
Oakland Suite - Mahone Bay Three Churches Vista
Price:€64 / night
Caribbean Style Backyard Bunkee
SUPERHOSTPrivate room
Caribbean Style Backyard Bunkee
Price:€49 / night
Chester Island Views
SUPERHOSTEntire flat
Chester Island Views
Price:€81 / night
Driftwood Cottage
SUPERHOSTEntire cottage
Driftwood Cottage
Price:€81 / night
Edgewater Suite - Mahone Bay Three Churches Vista
SUPERHOSTEntire guest suite
Edgewater Suite - Mahone Bay Three Churches Vista
Price:€64 / night
Big Red Roof (IMMACULATE,bathroom, Netflix coffee)
SUPERHOSTEntire guest suite
Big Red Roof (IMMACULATE,bathroom, Netflix coffee)
Price:€62 / night
Quarrie Cottage | Bright & airy in-town cottage
SUPERHOSTEntire cabin
Quarrie Cottage | Bright & airy in-town cottage
Price:€130 / night
Garden Loft Cottage on the Water
SUPERHOSTEntire cottage
Garden Loft Cottage on the Water
Price:€94 / night
Charming cozy cottage in the village of Chester
SUPERHOSTEntire cottage
Charming cozy cottage in the village of Chester
Price:€97 / night
Ocean Breezes/Ocean Views&Access/ 5 min/Mahone Bay
SUPERHOSTEntire guest house
Ocean Breezes/Ocean Views&Access/ 5 min/Mahone Bay
Price:€97 / night
Show all