The Best Chester Resorts from $85

A large, two-story house with a steeply pitched roof and a chimney.

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Recommended hotels in Chester

A modern living room with a flat-screen TV, a fireplace, a sofa set, and a large window with blinds.

1. Cozy 3-Bedroom, 2-Bath Home with Private Pool & Hot Tub, Chester Front Harbour

Chester

A hotel with a large outdoor patio area, multiple balconies, and a well-lit entrance.

2. Oak Island Resort & Conference Centre

Western Shore

Angela

$115 nightly

Nov 11 - Nov 12

Total with taxes and fees

A pathway leading to a house surrounded by lush greenery and a well-maintained garden.

3. Miller House By the Bay

mahone bay

David

$109 nightly

Nov 11 - Nov 12

Total with taxes and fees

A hotel room with two beds, a large window, and artwork on the walls.

4. The Homeport Motel

Lunenburg

Julie

$75 nightly

Nov 14 - Nov 15

Total with taxes and fees

A waterfront restaurant with outdoor seating and a gift shop.

5. The Dockside Inn & Restaurant

Lunenburg Waterfront

Wendy

$89 nightly

Nov 29 - Nov 30

Total with taxes and fees

A two-story house with a gabled roof and a front porch.

6. Fairmont House Bed & Breakfast

Mahone Bay

Marci

$143 nightly

Nov 10 - Nov 11

Total with taxes and fees

A bedroom with a wooden ceiling, a bed with white bedding, a nightstand, a dresser, a chair, a window with a view of trees, and a patterned rug.

7. Black Forest Cabins

Mahone Bay

Julie

$165 nightly

Nov 10 - Nov 11

Total with taxes and fees

A table with two wine glasses and a vase of flowers by a window overlooking a harbor.

8. Rum Runner Inn

Lunenburg Waterfront

Kathleen

$163 nightly

Nov 11 - Nov 12

Total with taxes and fees

A cozy living room with a grey sofa, a wooden staircase, a dining area with a white table and chairs, and a kitchen with white cabinets and a microwave.

9. Salt Shaker Deli & Inn

Lunenburg Waterfront

Myles

$161 nightly

Nov 11 - Nov 12

Total with taxes and fees

A view of a waterfront property with a dock and a small building.

10. Oceanfront Luxury Magical Views Sunset and Sunrise

Western Shore

Cynthia K G.

$218 nightly

Nov 24 - Nov 25

Total with taxes and fees

A wooden deck with a hot tub surrounded by trees.

11. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Windsor Road

Sandra

$170 nightly

Nov 17 - Nov 18

Total with taxes and fees

A small cabin with a deck, a door, and a window.

12. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Chester Basin

Suzanne

$140 nightly

Nov 8 - Nov 9

Total with taxes and fees

An indoor swimming pool with a blue slide, lounge chairs, and a red umbrella.

13. Best Western Plus Bridgewater Hotel & Convention Centre

Cookville

Michelle

$119 nightly

Nov 20 - Nov 21

Total with taxes and fees

A hotel room with two beds, a desk with a chair, a television, a coffee maker, and artwork on the walls.

14. Travelodge by Wyndham Bridgewater

Bridgewater

Wayne

$96 nightly

Nov 11 - Nov 12

Total with taxes and fees

A deck with a fire pit, outdoor seating, and a view of the ocean at sunset.

15. Lighthouse Lane Cottages

Indian Harbour

Kiana

$120 nightly

Nov 18 - Nov 19

Total with taxes and fees

A hotel room with a large bed, a desk with a television, a chair, and a window with curtains.

16. Days Inn & Conference Center by Wyndham Bridgewater

Bridgewater

Jeremy

$98 nightly

Nov 11 - Nov 12

Total with taxes and fees

A Victorian-style building with a prominent tower, large windows, and a balcony.

17. Bluenose Lodge

Lunenburg

John

$255 nightly

Nov 10 - Nov 11

Total with taxes and fees

A kitchen with wooden cabinets, a built-in oven, and a sink.

18. Red Barn Bed & Breakfast

Lunenburg

Kimberley K.

$124 nightly

Nov 12 - Nov 13

Total with taxes and fees

A small, two-story cabin with a deck, large windows, and a fireplace.

19. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Chester Basin

Marissa H.

$140 nightly

Nov 17 - Nov 18

Total with taxes and fees

A staircase with wooden balusters and a handrail, leading to a landing with a red door.

20. Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

Lunenburg

Patrick

$186 nightly

Nov 8 - Nov 9

Total with taxes and fees

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Top Chester Hotel Reviews

Days Inn & Conference Center by Wyndham Bridgewater

8/10 Good

"The room and amenities in the room were good, breakfast was good/sufficient, and restaurant was quaint. Gym on the other hand could definitely use some upgrades/additions. Although people probably aren’t spending a lot of time in the gym there, a decent machine for weights and/or some free weights. That’s really my only criticism for this place."

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

10/10 Excellent

"We loved every moment of our stay at the cottage! It is located perfectly- close to town but secluded enough that you feel you’re in your own little cove. Sitting outside you can enjoy pure silence, which is hard to come by these days. The provided s’mores package was a hit! We also enjoyed using the kayaks and exploring the area on the water. Despite being chilly out, we were still able to take advantage of all the outdoor amenities. Since we came at the start of the off season, many shops and restaurants in town were closed for the season, but that made town a lot less busy, which we enjoyed! The price of the cottage was very reasonable. We do plan on coming back in swimming season!"

The Dockside Inn & Restaurant

10/10 Excellent

"We had a wonderful room facing the harbor on the second floor. Fairly quiet because of the season but the view was wonderful--also helped that we had beautiful fall weather. Staff was excellent. They offered to let us use their washer and dryers when they were done with their daily needs when we inquired about doing a laundry. We chose to use a laundromat on outskirts of town where we were able to drop off and pick up later in day. Let us explore Lundenburg and its great selections of Victorian houses and the fishery museum. The restaurant while not fancy had a good selection of dishes. Would stay there again"

Black Forest Cabins

10/10 Excellent

"I have stayed at the Blackforest cabins four times now and every time we have a very clean positive experience. There has been great communication and easy instructions for checking in and checking out. I wish they had deals for reoccurring customers because it is pretty expensive to stay even for one night."

Find out more about Chester

Chester Resorts information

Number of reviews	3,244
Accommodation	0 Resorts
Lowest Price	$85
Highest Price	$291

Frequently asked questions

What can I expect from a resort vacation in Chester?

Expedia can help you find resorts and other lodging options that offer similar services and comforts. If you're having trouble finding a resort in Chester that works for you, try using the search filters to look for hotels, or search for properties that offer amenities like pools or all-inclusive packages. We make it simple to book great accommodations so you can focus on planning your trip itinerary.

What's a favorite resort in Chester?

Our highest-rated resort near Chester: "Luxurious Escapes Await: Private Hot Tubs and Kayaks at Norse Geodesic Retreat" - 11.4 mi (18.3 km) from Chester.

What can I do in Chester?

Check out the interesting exhibits at Lordly House Museum, or grab your golf clubs for a game at Chester Golf Club. For more to see in the area, you can spend time at Chester Art Center or Chester Playhouse.

What's the weather like in Chester?

The hottest months are usually August and July with an average temp of 62°F, while the coldest months are February and January with an average of 31°F. Average annual precipitation for Chester is 63 inches.

What's the best way to get to and around Chester?

Fly into Stanfield Intl. Airport (YHZ), which is located 42.8 mi (68.8 km) from the heart of the city. If you'd like to venture out around the area, you may want a rental car for your journey.

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Room 1

Check prices for these dates

Recommended hotels in Chester

1. Cozy 3-Bedroom, 2-Bath Home with Private Pool & Hot Tub, Chester Front Harbour

2. Oak Island Resort & Conference Centre

3. Miller House By the Bay

4. The Homeport Motel

5. The Dockside Inn & Restaurant

6. Fairmont House Bed & Breakfast

7. Black Forest Cabins

8. Rum Runner Inn

9. Salt Shaker Deli & Inn

10. Oceanfront Luxury Magical Views Sunset and Sunrise

11. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

12. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

13. Best Western Plus Bridgewater Hotel & Convention Centre

14. Travelodge by Wyndham Bridgewater

15. Lighthouse Lane Cottages

16. Days Inn & Conference Center by Wyndham Bridgewater

17. Bluenose Lodge

18. Red Barn Bed & Breakfast

19. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

20. Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

Top Chester Hotel Reviews

Days Inn & Conference Center by Wyndham Bridgewater

Bridgewater Hotel

Miller House By the Bay

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

Lighthouse Lane Cottages

Rum Runner Inn

The Dockside Inn & Restaurant

The Tuna Blue Inn and Restaurant

Black Forest Cabins

Find out more about Chester

Chester Resorts information

Frequently asked questions

Explore a world of travel with Expedia

Best Resorts in Chester

Check prices for these dates

Recommended hotels in Chester

1. Cozy 3-Bedroom, 2-Bath Home with Private Pool & Hot Tub, Chester Front Harbour

2. Oak Island Resort & Conference Centre

3. Miller House By the Bay

4. The Homeport Motel

5. The Dockside Inn & Restaurant

6. Fairmont House Bed & Breakfast

7. Black Forest Cabins

8. Rum Runner Inn

9. Salt Shaker Deli & Inn

10. Oceanfront Luxury Magical Views Sunset and Sunrise

11. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

12. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

13. Best Western Plus Bridgewater Hotel & Convention Centre

14. Travelodge by Wyndham Bridgewater

15. Lighthouse Lane Cottages

16. Days Inn & Conference Center by Wyndham Bridgewater

17. Bluenose Lodge

18. Red Barn Bed & Breakfast

19. Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

20. Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

Top Chester Hotel Reviews

Days Inn & Conference Center by Wyndham Bridgewater

Find out more about Chester

Chester Resorts information

Frequently asked questions

Explore a world of travel with Expedia