Chester Vacation Rentals

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Vacation Rentals in Chester

Family Home In the Heart of the Village of Chester

9.6 out of 10, Exceptional, (27)
"Spacious, clean, comfortable, and lots of room for people to spread out. We would happily return."
Family Home In the Heart of the Village of Chester

Black Forest Cabins

3.0 star property
10.0 out of 10, Exceptional, (4)
"Beautiful quiet cabins with local trails to enjoy and explore. The sauna was fantastic and we loved the decor! So easy to access our room. Highly recommend!"
The price is CA $312
CA $390 total
includes taxes & fees
Sep 1 - Sep 2
Black Forest Cabins

Oakhill Pines Campground

3.0 star property
9.0 out of 10, Wonderful, (4)
"Awesome place for a family stay! Cabin was great, the pool was nice, facilities were clean and all working. But the best part was the vibe; calm and quiet, but not too quiet. We wish we had longer to stay and enjoy! "
The price is CA $119
CA $136 total
includes taxes & fees
Aug 4 - Aug 5
Oakhill Pines Campground

Oceanfront 3-Bedroom Captain's House

10.0 out of 10, Exceptional, (19)
"Very clean, comfy, great water views. Recommended!"
Oceanfront 3-Bedroom Captain's House

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

10.0 out of 10, Exceptional, (1)
"Great location just outside of Lunenburg, quiet and remote. Beautiful inside!"
The price is CA $275
CA $415 total
includes taxes & fees
Aug 5 - Aug 6
Luxury lakefront dome with private beach, close to nature and town!

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

10.0 out of 10, Exceptional, (97)
"Property was wonderful, love Lunenburg and area would definitely return!!!"
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

Wilson's Coastal Club - C3

10.0 out of 10, Exceptional, (6)
"It's great when all goes well, but it's truly a blessing when things go wrong and your host takes care of you! Our hot water froze our first night and Jessica and Kyle were so lovely and helpful. Really enjoyed our stay and hope to come back again next year. "
The price is CA $359
CA $480 total
includes taxes & fees
Aug 12 - Aug 13
Wilson's Coastal Club - C3

Ocean front cottage in the heart of Hubbards.

9.8 out of 10, Exceptional, (46)
"This place was perfect for our little family stay! We enjoyed watching the boats from the deck and theres lots to do in the area. The hosts are lovely :)"
Ocean front cottage in the heart of Hubbards.

Spruce Bell Tent near Peggy's Cove

The price is CA $120
CA $196 total
includes taxes & fees
Aug 3 - Aug 4
Spruce Bell Tent near Peggy's Cove

Wilson's Coastal Club - C2

10.0 out of 10, Exceptional, (3)
"Great cottage. Exactly as advertised - cozy furniture, lovely surroundings and gardens, easy parking. The beds are exceptionally comfy! Would stay again!"
The price is CA $299
CA $400 total
includes taxes & fees
Sep 1 - Sep 2
Wilson's Coastal Club - C2

Beautiful Lakefront Home with 5 Bed/3 Baths, WiFi, tons of amenities!

9.8 out of 10, Exceptional, (28)
"Great house with basics to make it easy to stay."
Beautiful Lakefront Home with 5 Bed/3 Baths, WiFi, tons of amenities!

Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove

10.0 out of 10, Exceptional, (76)
"Everything about our trip and this property was amazing. The location, the peace, the scenery, etc. exceeded our expectations. The house was perfect and so comfortable. We hope to be back soon! "
Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove

The Land Yacht – Indoor Pool, Hot Tub, Solarium Lounge & Sublime Ocean Views

9.8 out of 10, Exceptional, (220)
"We had an absolutely wonderful time on the Land Yacht, the kids used the pool everyday and we all thoroughly enjoyed the perfect weather from the solarium :) The Land Yacht in an incredible spot and we will definitely be back again."
The Land Yacht – Indoor Pool, Hot Tub, Solarium Lounge & Sublime Ocean Views

Moonlight Cottage

9.8 out of 10, Exceptional, (11)
"Loved getting to come stay at the house that was the Grey Gull on Haven the TV show! The host was great with communicating and our stay was awesome."
Moonlight Cottage

Mahone Bay Hide-Away

10.0 out of 10, Exceptional, (80)
"Great little cottage. It was very clean and well equipped as well as nicely decorated. The man that met us there seemed very nice and helpful as well. "
Mahone Bay Hide-Away

Mahone Bay Town Center 2 Bedroom Apt. - Steps to Everything - Vacation Oasis

10.0 out of 10, Exceptional, (27)
"They thought of everything. It was great"
Mahone Bay Town Center 2 Bedroom Apt. - Steps to Everything - Vacation Oasis

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

7.8 out of 10, Good, (17)
"This property was great for our one night stay as a group attending a show at the shore club. The patio and view is wonderful! Owner was in contact very quickly which was very much appreciated. "
The price is CA $200
CA $261 total
includes taxes & fees
Aug 27 - Aug 28
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

Sandy beaches, big trees, lovely 3BR lodge - private. 10 km to Mahone Bay area

7.8 out of 10, Good, (9)
"Beautiful quiet place in beautiful nature"
Sandy beaches, big trees, lovely 3BR lodge - private. 10 km to Mahone Bay area

Wilson's Coastal Club - C1

10.0 out of 10, Exceptional, (3)
"Amazing spot! Gorgeous location, staff really friendly and helpful and we had such a relaxing weekend. Highly recommend!"
Wilson's Coastal Club - C1

Unique Ocean View Hilltop Retreat

10.0 out of 10, Exceptional, (170)
"We loved our stay at the Hilltop retreat. The architecture and design caught our attention, and the views out from the hilltop kept us enraptured. Proximity to Lunenburg amenities is great, and we enjoyed the farmer’s market nearby. Really a relaxing and lovely stay."
Unique Ocean View Hilltop Retreat
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

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?

Family Home In the Heart of the Village of Chester: Visitors give good reviews to this Chester vacation home rental, which is located near the beach and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 5 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the books in this rental home to help you unwind.

How many vacation rentals will I find in Chester?

Choose from 11 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.