Chester Vacation Rentals from $169: Search Short-Term Rentals

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Our top choices for Chester vacation rentals

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.

1. Black Forest Cabins

Mahone Bay

Julie

$259 nightly

Sep 30 - Oct 1

Total with taxes and fees

A wooden door with a view of an outdoor deck and a chair.

2. Oakhill Pines Campground

Oak Hill

David

A wooden deck with a hot tub surrounded by trees.

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

Windsor Road

Carol

$161 nightly

Oct 11 - Oct 12

Total with taxes and fees

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

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

Chester Basin

Suzanne

$161 nightly

Sep 30 - Oct 1

Total with taxes and fees

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

5. Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,

Western Shore

Kirby D.

$363 nightly

Sep 30 - Oct 1

Total with taxes and fees

A residential area with a house, a swimming pool, and a marina with boats.

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

Hubbards

Angela C.

$393 nightly

Sep 30 - Oct 1

Total with taxes and fees

A bright living room with a white sofa, a coffee table, and a potted plant.

7. One bedroom fully equipped Mahone Bay luxury cottage

Mahone Bay

Dianne T.

$203 nightly

Oct 17 - Oct 18

Total with taxes and fees

A porch with colorful Adirondack chairs and a wooden deck.

8. Log Cabin #1 - Hubbards Beach

Hubbards

Lisa R.

$309 nightly

Sep 30 - Oct 1

Total with taxes and fees

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

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

Chester Basin

francesco c.

$161 nightly

Oct 12 - Oct 13

Total with taxes and fees

A modern kitchen with white cabinetry, a wooden countertop, and a large mirror.

10. Mahone Bay Hide-Away

Mahone Bay

Richard

$204 nightly

Oct 9 - Oct 10

Total with taxes and fees

A tented accommodation with a bed, two chairs, and a view of a lake.

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

Lunenburg

LISA

$263 nightly

Oct 4 - Oct 5

Total with taxes and fees

A small white cabin with green trim and a porch, surrounded by greenery.

12. Orchard Cabin #4 - Hubbards Beach

Hubbards

Nancy O.

$197 nightly

Sep 30 - Oct 1

Total with taxes and fees

A dock with boats, a clear blue lake, and a forested island.

13. Mermaid's Retreat - Caribou Lake Cottage!

Mahone Bay

Betty

$231 nightly

Sep 30 - Oct 1

Total with taxes and fees

A sunset view through a window with bare trees and a distant shoreline.

14. 4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

Hubbards

Joanne

$148 nightly

Oct 5 - Oct 6

Total with taxes and fees

A spacious living room with a white sofa, wooden coffee table, and a rustic wooden chest. A wooden staircase leads to another room.

15. Cozy Cape Located In The Beautiful Seaside Town of Mahone Bay

Mahone Bay

Brauna R.

$310 nightly

Oct 6 - Oct 7

Total with taxes and fees

A wooden deck with a view of a lake and trees.

16. Beach Cottage - Oak Hollow - Hubbards Beach

Hubbards

"Jared (the owner) made our stay at Hubbards beach one we wont soon forget. The staff accommodated our every need, going above and beyond to secure us provisions when all the shops were closed for canada day. The cottage (oak hollow) was spacious, comfortably sleeping 5 adults, with a rustic and comfortable decor. The fireplace in the cottage saw a lot of use and was fully stocked with wood at no cost. Steps from the gorgeous hubbards beach, this spot had no shortage of activities to keep us...

CHRISTIAN P.

$392 nightly

Oct 18 - Oct 19

Total with taxes and fees

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

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

Boutiliers Point

Adele S.

$183 nightly

Oct 4 - Oct 5

Total with taxes and fees

18. Log Cabin #2 - Hubbards Beach

Hubbards

Jody K.

$308 nightly

Oct 8 - Oct 9

Total with taxes and fees

A calm lake with boats docked at the pier, surrounded by trees.

19. Lake Mushamush Cottage!

Lower Northfield

Rita

$202 nightly

Sep 30 - Oct 1

Total with taxes and fees

A covered outdoor deck with a glass table and chairs, overlooking a lake surrounded by trees.

20. Beach Cottage - Yellow Birches - Hubbards Beach

Hubbards

"Hubbard’s is such a great little area and the beach is beautiful. I come here every summer and have stayed in most of these cottages. Cottage had everything you need, lots of towels, extra blankets, water cooler, etc. Staff is extremely friendly at check in, garbage pickup, and all the restaurants. Our cottage had a beautiful view of the pond and ocean, a good sized deck with barbecue, a nice lawn area for activities, and space for parking. It had a very rustic cottage-like vibe which is what I...

Alea L.

$375 nightly

Sep 30 - Oct 1

Total with taxes and fees

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Top Chester Hotel Reviews

Travelodge by Wyndham Bridgewater

8/10 Good

"The room was large, bedding was clean, and the bed was very comfy. We were in a ground floor room, patio doors were extremely heavy and I could not even close one of them as it wouldn't slide. Walls were thin, we could here people talking in the room next door. It was an okay place to stay, I was happy the rooms were clean and the beds were comfortable."

The Homeport Motel

10/10 Excellent

"We enjoyed our one night stay. The rooms are newly renovated and were very clean. The furniture all newer with a fridge with a separate freezer, comfy bed, microwave, toaster extra sink, plates and utensils. Roku TV, heated towel rack and the towels were fluffy! It is not right downtown but a 20 min walk which we were good with. The front desk person was amazing in helping us navigate some issues with our booking which was not the motel's fault."

Bridgewater Hotel

8/10 Good

"It’s a good, clean place to stay in a great location. Staff was helpful with all our questions, check in was quick and easy, the room was basic and clean, parking was easy. Not much for amenities or activities at the hotel, but that’s not why we stayed there. Price was very reasonable. Quick access to many different areas of interest nearby. Would stay there again."

Find out more about Chester

Everything you need to know about Chester vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chester vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chester vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chester vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chester. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Chester in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $169 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chester rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chester vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chester. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Are there vacation rentals in Chester?

Yes, there are vacation rentals close to the most popular sights in Chester, or you can choose a secluded option if you'd like a relaxing place to stay. Chester is known for its golf courses and theaters. Make sure you have time to check out the entertainment choices and art during your trip.

What are some of the best vacation rentals in Chester?

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort: This vacation 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Chester?

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

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 vacation rental in Chester like?

Vacation rentals are privately owned properties you can stay in for short or long periods in Chester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a family trip or a small group gathering.

Chester Vacation Rentals

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Check prices for these dates

Our top choices for Chester vacation rentals

1. Black Forest Cabins

2. Oakhill Pines Campground

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

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

5. Luxury Oceanfront Retreat in Chester close to Mahone Bay, Lunenburg,

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

7. One bedroom fully equipped Mahone Bay luxury cottage

8. Log Cabin #1 - Hubbards Beach

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

10. Mahone Bay Hide-Away

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

12. Orchard Cabin #4 - Hubbards Beach

13. Mermaid's Retreat - Caribou Lake Cottage!

14. 4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

15. Cozy Cape Located In The Beautiful Seaside Town of Mahone Bay

16. Beach Cottage - Oak Hollow - Hubbards Beach

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

18. Log Cabin #2 - Hubbards Beach

19. Lake Mushamush Cottage!

20. Beach Cottage - Yellow Birches - Hubbards Beach

Find vacation rentals that suit your style

Top Chester Hotel Reviews

Travelodge by Wyndham Bridgewater

Find out more about Chester

Explore a world of travel with Expedia

Frequently asked questions

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