Chester Holiday Rentals: Short-Term Accommodations for Rent

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Our top choices for Chester holiday rentals

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 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.

2. Black Forest Cabins

Mahone Bay

Julie

HK$1,479 total

includes taxes & fees

8 Nov - 9 Nov

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

3. Oceanfront Luxury Magical Views Sunset and Sunrise

Western Shore

Cynthia K G.

HK$2,032 total

includes taxes & fees

29 Nov - 30 Nov

A wooden deck with a hot tub surrounded by trees.

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

Windsor Road

Sandra

HK$1,520 total

includes taxes & fees

17 Nov - 18 Nov

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

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

Chester Basin

Suzanne

HK$1,252 total

includes taxes & fees

12 Nov - 13 Nov

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

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

Lunenburg

Patrick

HK$1,746 total

includes taxes & fees

6 Nov - 7 Nov

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

7. Red Barn Bed & Breakfast

Lunenburg

Kimberley K.

HK$1,109 total

includes taxes & fees

6 Nov - 7 Nov

A lakeside property with a sandy beach, lounge chairs, and a dock.

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

Boutiliers Point

Kristopher H.

HK$1,446 total

includes taxes & fees

6 Nov - 7 Nov

A tented accommodation with a bed, a television, and a view of a body of water.

9. Luxury lakefront dome with private beach, close to nature and town!

Lunenburg

Sandie

HK$2,111 total

includes taxes & fees

8 Nov - 9 Nov

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

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

Chester Basin

Marissa H.

HK$1,252 total

includes taxes & fees

16 Nov - 17 Nov

A cozy cabin with a rustic interior, a wooden floor, a stove, a chair, and a view of a lake.

11. Mermaid's Retreat - Caribou Lake Cottage!

Mahone Bay

Josh

HK$2,082 total

includes taxes & fees

6 Nov - 7 Nov

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

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

Ingramport

Victoria W.

HK$2,858 total

includes taxes & fees

6 Nov - 7 Nov

A wooden cabin and a geodesic dome structure with seating and a fire pit, surrounded by a forest.

13. Pet-Friendly Glamping Dome close to Peggy’s Cove!

Seabright

Judy

HK$1,989 total

includes taxes & fees

6 Nov - 7 Nov

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

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

Boutiliers Point

Christopher

HK$1,156 total

includes taxes & fees

12 Nov - 13 Nov

A room with a ceiling fan, a large window with blinds, a sofa, and a small table with decorative items.

15. Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.

Bridgewater

Christina

HK$1,785 total

includes taxes & fees

10 Nov - 11 Nov

A cozy living room with a grey sofa, a white coffee table, and a wooden ceiling.

16. Oceanview 3-Bedroom Cottage | Fireplace | Sauna | Near Halifax

Boutiliers Point

Joanna

HK$1,643 total

includes taxes & fees

12 Nov - 13 Nov

A dining area with a wooden table, chairs, and a chandelier. There is a living room with a sofa and a TV in the background.

17. Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater

Bridgewater

Cheriee

HK$1,995 total

includes taxes & fees

13 Nov - 14 Nov

A wooden deck with a sauna, overlooking a beach with rocks and a calm sea.

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

Boutiliers Point

Dawn

HK$1,492 total

includes taxes & fees

17 Nov - 18 Nov

19. Coastal Studio Suite Steps from the Ocean | pet friendly

Boutiliers Point

HK$1,051 total

includes taxes & fees

12 Nov - 13 Nov

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Top Chester Hotel Reviews

The Homeport Motel

10/10 Excellent

"It was queit and quite cozy. Amazing night sleep!"

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"

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

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Frequently asked questions

Are there holiday rentals in Chester?

Yes, there are holiday rentals close to the most popular sights in Chester, or you can select a more secluded option if you're looking for a relaxing stay. Chester is known for its golf courses and theatres. Make sure you have time to check out the entertainment choices and art during your trip.

What are some of the best holiday rentals that Chester has to offer?

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort: This holiday home rental outside Chester is located by the ocean, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

How many holiday rentals will I find in Chester?

Choose from 16 Expedia holiday rentals in Chester for a memorable holiday.

What’s there to see and do in Chester?

Cultural attractions to visit include Chester Playhouse and Lordly House Museum. Chester Art Center and Chester Golf Club are other places to visit while you're in town.

What’s a holiday rental in Chester like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chester. Holiday rentals offer extras such as WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a clean environment, holiday rentals can provide a sense of privacy away from public hotel lifts and busy reception areas while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips.

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Check prices for these dates

Our top choices for Chester holiday rentals

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

2. Black Forest Cabins

3. Oceanfront Luxury Magical Views Sunset and Sunrise

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

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

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

7. Red Barn Bed & Breakfast

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

9. Luxury lakefront dome with private beach, close to nature and town!

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

11. Mermaid's Retreat - Caribou Lake Cottage!

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

13. Pet-Friendly Glamping Dome close to Peggy’s Cove!

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

15. Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.

16. Oceanview 3-Bedroom Cottage | Fireplace | Sauna | Near Halifax

17. Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater

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

19. Coastal Studio Suite Steps from the Ocean | pet friendly

Find holiday rentals that suit your style

Top Chester Hotel Reviews

The Homeport Motel

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

Best Western Plus Bridgewater Hotel & Convention Centre

The Dockside Inn & Restaurant

Find out more about Chester

Frequently asked questions

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