Chester Vacation Rentals from $127: Search Short-Term Rentals

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Our top choices for Chester vacation 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

$165 nightly

Nov 15 - Nov 16

Total with taxes and fees

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.

$218 nightly

Nov 24 - Nov 25

Total with taxes and fees

A wooden deck with a hot tub surrounded by trees.

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

Windsor Road

Sandra

$170 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

$140 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

$186 nightly

Nov 7 - Nov 8

Total with taxes and fees

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

7. Red Barn Bed & Breakfast

Lunenburg

Kimberley K.

$124 nightly

Nov 6 - Nov 7

Total with taxes and fees

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.

$158 nightly

Nov 6 - Nov 7

Total with taxes and fees

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

Maxime

$236 nightly

Nov 11 - Nov 12

Total with taxes and fees

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.

$140 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

$233 nightly

Nov 11 - Nov 12

Total with taxes and fees

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.

$312 nightly

Nov 6 - Nov 7

Total with taxes and fees

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

$217 nightly

Nov 6 - Nov 7

Total with taxes and fees

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

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

Boutiliers Point

Christopher

$126 nightly

Nov 6 - Nov 7

Total with taxes and fees

A living room with a sofa, a table with a plant, and a window with blinds.

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

Bridgewater

Christina

$191 nightly

Dec 4 - Dec 5

Total with taxes and fees

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

$179 nightly

Nov 6 - Nov 7

Total with taxes and fees

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

$217 nightly

Nov 13 - Nov 14

Total with taxes and fees

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

$163 nightly

Nov 7 - Nov 8

Total with taxes and fees

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

Boutiliers Point

$115 nightly

Nov 6 - Nov 7

Total with taxes and fees

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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

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 $127 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. 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 vacation rentals that suit your style

Top Chester Hotel Reviews

The Homeport Motel

Find out more about Chester

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