Chester Vacation Rentals

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Our top choices for Chester vacation rentals

Black Forest Cabins

Black Forest Cabins
3.0 star property
Mahone Bay
9.6 out of 10, Exceptional, (27 reviews)
"Wonderful cabins and well located. "
Canada
Jonathan
$156 nightly
The price is $178
May 26 - May 27
Total with taxes and fees
Black Forest Cabins

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

Oceanview Cottage | Private Wood-Fired Hot Tub | Sauna | Near Halifax
Boutiliers Point
10.0 out of 10, Exceptional, (12 reviews)
"It was cleaned and cozy stay with beautiful lake view"
Canada
Vikrant D.
$193 nightly
The price is $225
May 10 - May 11
Total with taxes and fees
Oceanview Cottage | Private Wood-Fired Hot Tub | Sauna | Near Halifax

Red Roof Bed & Breakfast

Red Roof Bed & Breakfast
Lunenburg
9.6 out of 10, Exceptional, (9 reviews)
"We enjoyed our stay very much! "
Canada
Kimberley K.
$175 nightly
The price is $199
May 13 - May 14
Total with taxes and fees
Red Roof Bed & Breakfast

Lake Mushamush Cottage!

Lake Mushamush Cottage!
Lower Northfield
9.6 out of 10, Exceptional, (4 reviews)
"Beautiful spot we had the best time!!"
Canada
Patricia C.
$216 nightly
The price is $247
May 13 - May 14
Total with taxes and fees
Lake Mushamush Cottage!

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Chester Basin
10.0 out of 10, Exceptional, (20 reviews)
"Hot tub is Devine, everything is clean and thoughtfully provided. Basket of snacks was a sweet treat! We enjoyed the large deck and privacy very much ♥️we will definitely be back "
Canada
Suzanne
$130 nightly
The price is $148
May 13 - May 14
Total with taxes and fees
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

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

Luxury lakefront dome with private beach, close to nature and town!
Lunenburg
9.8 out of 10, Exceptional, (10 reviews)
"Perfect spot for a peaceful getaway with a great view. "
Canada
Alan L.
$191 nightly
The price is $218
May 13 - May 14
Total with taxes and fees
Luxury lakefront dome with private beach, close to nature and town!

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

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort
Hubbards
8.2 out of 10, Very Good, (31 reviews)
"Great stay"
Canada
Nigel F.
$156 nightly
The price is $178
May 21 - May 22
Total with taxes and fees
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise
Western Shore
9.6 out of 10, Exceptional, (21 reviews)
"Short stay, unfortunately, but I’ll definitely be back. "
Canada
Laird N.
$217 nightly
The price is $254
May 13 - May 14
Total with taxes and fees
Oceanfront Luxury Magical Views Sunset and Sunrise

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

Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)
Lunenburg
8.8 out of 10, Excellent, (8 reviews)
"Close to town , clean and comfortable "
United States
Tom D.
$199 nightly
The price is $227
May 13 - May 14
Total with taxes and fees
Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

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

Pet-Friendly Glamping Dome close to Peggy’s Cove!
Seabright
10.0 out of 10, Exceptional, (5 reviews)
"It was a pleasure to stay here! It's well located, very cozy, spacious, and full of amenities. We felt nestled in a restful, secluded forest, yet not far off the main road. Our dog loved it here."
United States
Claudia Franey J.
$216 nightly
The price is $253
May 11 - May 12
Total with taxes and fees
Pet-Friendly Glamping Dome close to Peggy’s Cove!

King Bed Apt in Bridgewater near River and Trails

King Bed Apt in Bridgewater near River and Trails
Bridgewater
$137 nightly
The price is $158
May 10 - May 11
Total with taxes and fees
King Bed Apt in Bridgewater near River and Trails

One bedroom fully equipped Mahone Bay luxury cottage

One bedroom fully equipped Mahone Bay luxury cottage
Mahone Bay
10.0 out of 10, Exceptional, (105 reviews)
"Fantastic hosts and wonderful accommodation! "
Canada
Karen D.
$235 nightly
The price is $268
Jun 2 - Jun 3
Total with taxes and fees
One bedroom fully equipped Mahone Bay luxury cottage

Orchard Cabin #4 - Hubbards Beach

Orchard Cabin #4 - Hubbards Beach
Hubbards
7.4 out of 10, Good, (6 reviews)
"We were upgrated and the property was very nice and comfortable. Very clean too. "
United States
Ghislaine L.
$201 nightly
The price is $234
May 17 - May 18
Total with taxes and fees
Orchard Cabin #4 - Hubbards Beach

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Windsor Road
9.8 out of 10, Exceptional, (9 reviews)
"The cleanliness was impeccable, the hospitality was lovely. Everything one needs while away from home was supplied and then some ! Would definitely visit again !"
Canada
Carol
$159 nightly
The price is $181
May 18 - May 19
Total with taxes and fees
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Romantic Oceanfront Retreat - Hot tub

Romantic Oceanfront Retreat - Hot tub
South Shore
9.2 out of 10, Wonderful, (12 reviews)
"A very nice location"
Canada
Evelyn K.
$320 nightly
The price is $364
May 19 - May 20
Total with taxes and fees
Romantic Oceanfront Retreat - Hot tub

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

Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater
Bridgewater
9.4 out of 10, Exceptional, (3 reviews)
"As described and in a great location!"
United States
Erin E.
$227 nightly
The price is $265
May 11 - May 12
Total with taxes and fees
Welcome to our cozy/charming 2 Bedroom 1 Bath Apartment in Central Bridgewater

Log Cabin #1 - Hubbards Beach

Log Cabin #1 - Hubbards Beach
Hubbards
9.6 out of 10, Exceptional, (4 reviews)
"A wonderful cottage with character!! Comfy beds, nice pillows! Very rustic, very peaceful"
Canada
Lisa R.
$313 nightly
The price is $364
May 17 - May 18
Total with taxes and fees
Log Cabin #1 - Hubbards Beach

Abigael’s Apt Suite 1 BR 2 BED in Central Bridgewater

Abigael’s Apt Suite 1 BR 2 BED in Central Bridgewater
Bridgewater
9.0 out of 10, Wonderful, (2 reviews)
"Nice to have all the appliances and be able to do our laundry. Good location, Wilma was a responsive host. They need better signage - the building has a barber shop in it and 3 people coming for a haircut ended up knocking on our door because they couldn't find the entrance, which is through the Bubble Tea shop. Noisy in the day time but okay for sleeping."
Canada
Jeannie T.
$178 nightly
The price is $208
May 13 - May 14
Total with taxes and fees
Abigael’s Apt Suite 1 BR 2 BED in Central Bridgewater

Luxury Coastal Dome - Private Hot Tub, Oceanfront Deck, Firepit & Parking

Luxury Coastal Dome - Private Hot Tub, Oceanfront Deck, Firepit & Parking
LaHave
10.0 out of 10, Exceptional, (11 reviews)
"Great experience "
Canada
Nathan D.
$370 nightly
The price is $430
May 13 - May 14
Total with taxes and fees
Luxury Coastal Dome - Private Hot Tub, Oceanfront Deck, Firepit & Parking

Juniper Bell Tent near Peggy's Cove

Juniper Bell Tent near Peggy's Cove
East Dover
8.8 out of 10, Excellent, (3 reviews)
"Good for a nights stay and close to Peggy’s cove. Comfy and enough space"
Canada
Pamela M.
$126 nightly
The price is $147
May 28 - May 29
Total with taxes and fees
Juniper Bell Tent near Peggy's Cove
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews

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 $152 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.

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?

The Chester House. Seaside in the village, with private wharf: Visitors give good reviews to this Chester vacation home rental, which is located on the beach and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 3 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. Tancook Island 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.