Holiday Rentals in Chester

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Our top choices for Chester holiday rentals

Black Forest Cabins

Black Forest Cabins
3.0 star property
Mahone Bay
9.6 out of 10, Exceptional, (25 reviews)
"Wonderful cabins and well located. "
Canada
Jonathan
The price is €167
includes taxes & fees
3 May - 4 May
Black Forest Cabins

Romantic Oceanfront Studio | Private Hot Tub | Fireplace | Near Halifax

Romantic Oceanfront Studio | Private Hot Tub | Fireplace | Near Halifax
Boutiliers Point
10.0 out of 10, Exceptional, (12 reviews)
"The cabin was very private and it was nice having the hot tub on our front deck."
Canada
Jane T.
The price is €168
includes taxes & fees
30 Apr - 1 May
Romantic Oceanfront Studio | Private Hot Tub | Fireplace | Near Halifax

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.
The price is €183
includes taxes & fees
4 May - 5 May
Luxury lakefront dome with private beach, close to nature and town!

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.
The price is €211
includes taxes & fees
1 May - 2 May
Lake Mushamush Cottage!

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.
The price is €172
includes taxes & fees
6 May - 7 May
Red Roof Bed & Breakfast

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

Tiny home in Chester Nova Scotia. Hosted by Dordean Suites
Chester Basin
9.8 out of 10, Exceptional, (15 reviews)
"There’s so much about Dordéan Suites to like: a contemporary, fun alternative to large, impersonal corporate roadside hotel. Loved our place, loved our stay! "
United States
Karil
The price is €137
includes taxes & fees
10 May - 11 May
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

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.
The price is €216
includes taxes & fees
29 Apr - 30 Apr
Pet-Friendly Glamping Dome close to Peggy’s Cove!

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
The price is €167
includes taxes & fees
27 May - 28 May
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

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

Oceanview 3-Bedroom Cottage | Fireplace | Sauna | Near Halifax
Boutiliers Point
9.4 out of 10, Exceptional, (10 reviews)
"Great cottage and location is amazing! "
Canada
Joanna
The price is €217
includes taxes & fees
30 Apr - 1 May
Oceanview 3-Bedroom Cottage | Fireplace | Sauna | Near Halifax

Indulge in luxurious bliss : private Hot Tub, kayaking. So much more

Indulge in luxurious bliss : private Hot Tub, kayaking. So much more
Chester
9.0 out of 10, Wonderful, (2 reviews)
"It was the perfect get away for myself after a rough week at work! Highly recommend. "
Canada
Michelle L.
The price is €227
includes taxes & fees
11 May - 12 May
Indulge in luxurious bliss : private Hot Tub, kayaking. So much more

Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise
Western Shore
9.6 out of 10, Exceptional, (20 reviews)
"Excellent unit and very clean.The view was awesome.Highly recommended for a wonderful place to stay."
Canada
John S.
The price is €214
includes taxes & fees
6 May - 7 May
Oceanfront Luxury Magical Views Sunset and Sunrise

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.
The price is €130
includes taxes & fees
28 May - 29 May
Juniper Bell Tent near Peggy's Cove

Backyard Bliss 1BR Suite near River and Trails

Backyard Bliss 1BR Suite near River and Trails
Bridgewater
10.0 out of 10, Exceptional, (1 review)
"Perfect place to stay. We will be back for sure."
Canada
Geoff M.
The price is €123
includes taxes & fees
10 May - 11 May
Backyard Bliss 1BR Suite near River and Trails

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.
The price is €361
includes taxes & fees
29 Apr - 30 Apr
Luxury Coastal Dome - Private Hot Tub, Oceanfront Deck, Firepit & Parking

Relaxing King Bed Suite Close to Lunenburg Harbour (Suite 2)

Relaxing King Bed Suite Close to Lunenburg Harbour (Suite 2)
Lunenburg
9.6 out of 10, Exceptional, (4 reviews)
"It is a lovely place to stay! Very clean, very inviting."
Canada
Danette R.
The price is €178
includes taxes & fees
29 Apr - 30 Apr
Relaxing King Bed Suite Close to Lunenburg Harbour (Suite 2)

Orchard Cabin #4 - Hubbards Beach

Orchard Cabin #4 - Hubbards Beach
Hubbards
7.4 out of 10, Good, (6 reviews)
"Very cute property with a nice location. "
United States
Nancy O.
The price is €203
includes taxes & fees
17 May - 18 May
Orchard Cabin #4 - Hubbards Beach

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.
The price is €176
includes taxes & fees
21 May - 22 May
4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort

Sunny Bachelor with Balcony near River & Trails

Sunny Bachelor with Balcony near River & Trails
Bridgewater
The price is €128
includes taxes & fees
4 May - 5 May
Sunny Bachelor with Balcony near River & Trails

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.
The price is €178
includes taxes & fees
11 May - 12 May
Abigael’s Apt Suite 1 BR 2 BED in Central Bridgewater

Coastal Gale

Coastal Gale
Lunenburg
9.8 out of 10, Exceptional, (8 reviews)
"This home is very comfortable & the location was convenient for us. The scenery is beautiful and we enjoyed the hot tube. "
Canada
Linda G.
The price is €433
includes taxes & fees
3 May - 4 May
Coastal Gale
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chester holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Chester holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chester holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chester holiday rentals we have selected for you start as low as €123 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chester rentals

At Expedia, we put the best Chester holiday 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 holiday.

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 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?

The Chester House. Seaside in the village, with private wharf: This highly rated holiday home rental in Chester is located on the beach, and has a patio, a garden and a BBQ 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 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. Tancook Island 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.