Chester Cottages from CA $219

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

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Our top choices for Chester cottages

A sauna with a view of the sea, wooden walls, and a stone heater.

1. Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax

Boutiliers Point

Kristopher H.

CA $271 total

includes taxes & fees

Nov 1 - Nov 2

A dock with chairs, a small building with a 'WELCOME' sign, and a lake view.

2. Mermaid's Retreat - Caribou Lake Cottage!

Mahone Bay

Josh

CA $391 total

includes taxes & fees

Oct 31 - Nov 1

A wooden deck with a glass-top table, wicker chairs, and a small umbrella.

3. Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail

Ingramport

Victoria W.

CA $511 total

includes taxes & fees

Oct 31 - Nov 1

A geodesic dome tent with a wooden frame and a transparent covering, situated in a forested area with trees and a cloudy sky in the background.

4. Indulge in luxurious bliss : private Hot Tub, kayaking. So much more

Chester

Michelle L.

CA $358 total

includes taxes & fees

Nov 1 - Nov 2

A dining table with blue plates, a bottle, and a glass.

5. Coastal Bunkie Retreat | Near Halifax | Sauna Access | Private Beach

Boutiliers Point

Christopher

CA $219 total

includes taxes & fees

Oct 31 - Nov 1

A row of houses with a gravel driveway leading to a dock by the water.

6. SUN, SAND, OCEAN, in Hubbards. What more do you need?

Hubbards

Sue

CA $695 total

includes taxes & fees

Oct 31 - Nov 1

A wooden dock extending into a calm body of water with a clear view of a distant shoreline and trees.

7. Oceanfront 2-Bedroom Cottage | Private Hot Tub | Wood Stove | Near Halifax

Boutiliers Point

Sarah M.

CA $278 total

includes taxes & fees

Nov 5 - Nov 6

8. Romantic Oceanfront Cottage | Private Wood-Fired Hot Tub | Near Halifax

Boutiliers Point

Dawn

CA $280 total

includes taxes & fees

Nov 1 - Nov 2

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Top Chester Hotel Reviews

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"

Lighthouse Lane Cottages

10/10 Excellent

"I stayed here on my own during a rain storm and although I could not enjoy the patio, I was able to enjoy the cozy cabin, with the fire on and watch the ocean through the patio door. The location was very quite and so charming. I would have loved to have stayed longer and spent more time on the patio, looking at the unobstructed view! The cabin has great natural light, with loads of windows, a cute little kitchen with everything you would need. The bed was super cozy."

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

8/10 Good

"This is a wonderful location close enough to many attractions and isolated enough for a peaceful getaway. Deer roamed the property, kayaking for those who enjoy being on the water. Full windows across the front of this cottage offering a lovely view of the water, seagulls, night sky! You won’t find as many properties that are as clean and comfortable as here. It is a perfect place for two couples or four people. Your host Frank & Valerie are friendly, and all round nice people who will make your stay enjoyable! I had my 10 lb Cockapoo w me and she thoroughly enjoyed her stay as well. Plenty of places to go for a hike or leisurely walk. I visited Blue Rocks, two nearby beaches, Lunenberg, Mahone Bay on my way home where you can fill up with gas right in town. There are multiple cafes, restaurants & bistros if you prefer to eat out. A local grocery store in Lunenburg along the waterfront and another lovely one with a European flare in Rose Bay, look for the unusual and not those big chains. I visited from Oct 11 - 28, 2026, I had some beautiful days, some cooler day (I do enjoy sweater weather), so don’t hesitate to go as I did a little later in the season when the tourist traffic has calmed down. Many thanks to my hosts Frank & Valerie!"

Miller House By the Bay

8/10 Good

"This is a beautiful B&B and the owner is lovely. She is very chatty and helpful and made us breakfast in the morning. The location was also great! The only reason I didn't give five stars is because 'the hug' room was smaller than I anticipated. I knew it would be small, but it was quite tiny for two adults. I also didn't love that we had to share a bathroom with the rest of the guests but that's a personal thing. Would still stay here again!"

Find out more about Chester

Chester Cottages information

Number of reviews	289
Accommodation	54 Cottages
Lowest Price	CA $219
Highest Price	CA $695

Frequently asked questions

How much do cottages in Chester cost?

Expect to pay between CA $219 and CA $695 per night for cottages in Chester. Whatever your budget, a fantastic stay is just clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Why book your cottage in Chester with Expedia?

We think that a vacation should be stress-free, so if you're on the lookout for cottages in Chester at an affordable price, Expedia is here to help. Keep the budget in check and pick a thrifty option surrounded by wilderness, or splurge on a 5-star cottage to really spoil your favorite people.

How can I find cheap cottages in Chester?

Expedia is here to help you easily track down cheap cottages in Chester. To find a terrific stay in a few quick keystrokes, simply use our handy filter tool to tailor your search results by amenities, budget and star rating.

What is there to do in Chester near my cottage?

Chester has enough experiences and activities to keep you going for weeks (or months!), starting with Amicus Gallery. Chester Playhouse, Chester Golf Club and Tancook Island are other terrific attractions. If you have more time, Chester Art Center and St. Stephen's Church are nice finishing touches to your itinerary.

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Treat yourself

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Check prices for these dates

Our top choices for Chester cottages

1. Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax

2. Mermaid's Retreat - Caribou Lake Cottage!

3. Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail

4. Indulge in luxurious bliss : private Hot Tub, kayaking. So much more

5. Coastal Bunkie Retreat | Near Halifax | Sauna Access | Private Beach

6. SUN, SAND, OCEAN, in Hubbards. What more do you need?

7. Oceanfront 2-Bedroom Cottage | Private Hot Tub | Wood Stove | Near Halifax

8. Romantic Oceanfront Cottage | Private Wood-Fired Hot Tub | Near Halifax

9. Oceanview Cottage | Private Wood-Fired Hot Tub | Sauna | Near Halifax

10. Family-Friendly Oceanview Cottage | Private Hot Tub | Near Halifax

11. Romantic Oceanfront Studio | Private Hot Tub | Fireplace | Near Halifax

12. Luxury Oceanview Retreat | Private Hot Tub | Shared Sauna | Near Halifax

Find vacation rentals that suit your style

Top Chester Hotel Reviews

The Dockside Inn & Restaurant

Lighthouse Lane Cottages

Rum Runner Inn

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

Bridgewater Hotel

The Tuna Blue Inn and Restaurant

Best Western Plus Bridgewater Hotel & Convention Centre

Miller House By the Bay

Oak Island Resort & Conference Centre

Find out more about Chester

Chester Cottages information

Frequently asked questions

Explore a world of travel with Expedia

Search Chester Cottage Rentals from CA $219

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chester cottages

1. Oceanview 1-Bedroom Cottage | Private Hot Tub | Near Halifax

2. Mermaid's Retreat - Caribou Lake Cottage!

3. Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail

4. Indulge in luxurious bliss ￼: private Hot Tub, kayaking. So much more

5. Coastal Bunkie Retreat | Near Halifax | Sauna Access | Private Beach

6. SUN, SAND, OCEAN, in Hubbards. What more do you need?

7. Oceanfront 2-Bedroom Cottage | Private Hot Tub | Wood Stove | Near Halifax

8. Romantic Oceanfront Cottage | Private Wood-Fired Hot Tub | Near Halifax

9. Oceanview Cottage | Private Wood-Fired Hot Tub | Sauna | Near Halifax

10. Family-Friendly Oceanview Cottage | Private Hot Tub | Near Halifax

11. Romantic Oceanfront Studio | Private Hot Tub | Fireplace | Near Halifax

12. Luxury Oceanview Retreat | Private Hot Tub | Shared Sauna | Near Halifax

Find vacation rentals that suit your style

Top Chester Hotel Reviews

The Dockside Inn & Restaurant

Find out more about Chester

Chester Cottages information

Frequently asked questions

Explore a world of travel with Expedia

4. Indulge in luxurious bliss : private Hot Tub, kayaking. So much more