Search Holiday Rentals in Chester

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Save instantly and earn perks with One Key
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Our top choices for Chester holiday rentals

1. Cozy 3-Bedroom, 2-Bath Home with Private Pool & Hot Tub, Chester Front Harbour

Cozy 3-Bedroom, 2-Bath Home with Private Pool & Hot Tub, Chester Front Harbour
Chester
Cozy 3-Bedroom, 2-Bath Home with Private Pool & Hot Tub, Chester Front Harbour

2. Black Forest Cabins

Black Forest Cabins
3.0 star property
Mahone Bay
9.6 out of 10, Exceptional, (89 reviews)
"It was a cute and cozy stay. We would stay here again."
Canada
Julie
The price is £140
includes taxes & fees
9 Nov - 10 Nov
Black Forest Cabins

3. Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise
Western Shore
9.2 out of 10, Wonderful, (29 reviews)
"Excellent location with beautiful marina and ocean view from the property. Very well maintained with excellent host Holly."
United States
Cynthia K G.
The price is £187
includes taxes & fees
29 Nov - 30 Nov
Oceanfront Luxury Magical Views Sunset and Sunrise

4. 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, (23 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
The price is £120
includes taxes & fees
9 Nov - 10 Nov
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

5. 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, (18 reviews)
"Unique property. Cozy warm and welcoming from the get go. Owners would respond to questions within minutes. Accommodations were immaculate and had everything we needed. They've literally thought of everything. Can't wait to visit again"
Canada
Sandra
The price is £146
includes taxes & fees
15 Nov - 16 Nov
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

6. Red Barn Bed & Breakfast

Red Barn Bed & Breakfast
Lunenburg
9.4 out of 10, Exceptional, (13 reviews)
"We enjoyed our stay very much! "
Canada
Kimberley K.
The price is £107
includes taxes & fees
12 Nov - 13 Nov
Red Barn Bed & Breakfast

7. 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, (17 reviews)
"A lovely accommodation. The hot tub was a definite plus, especially after a day of travelling. Highly recommend this tiny home :)"
United States
Marissa H.
The price is £120
includes taxes & fees
15 Nov - 16 Nov
Tiny home in Chester Nova Scotia. Hosted by Dordean Suites

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

Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)
Lunenburg
9.0 out of 10, Wonderful, (14 reviews)
"Loved our stay. Nice and clean, quiet and peaceful. Amazing yard. Basics were excellent (Bed, Tv & facilities). Definitely recommend."
Canada
Patrick
The price is £156
includes taxes & fees
9 Nov - 10 Nov
Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

9. Romantic Oceanfront Cottage | Private Wood-Fired Hot Tub | Near Halifax

Romantic Oceanfront Cottage | Private Wood-Fired Hot Tub | Near Halifax
Boutiliers Point
10.0 out of 10, Exceptional, (18 reviews)
"Little over priced for the early check out"
Canada
meredith
The price is £142
includes taxes & fees
15 Nov - 16 Nov
Romantic Oceanfront Cottage | Private Wood-Fired Hot Tub | Near Halifax

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

Coastal Bunkie Retreat | Near Halifax | Sauna Access | Private Beach
Boutiliers Point
10.0 out of 10, Exceptional, (1 review)
"Awesome cabin, great staff who were welcoming and helpful. Great location close to all major attractions"
Canada
Christopher
The price is £111
includes taxes & fees
9 Nov - 10 Nov
Coastal Bunkie Retreat | Near Halifax | Sauna Access | Private Beach

11. Downtown Bridgewater Suite near River and Trails

Downtown Bridgewater Suite near River and Trails
Bridgewater
9.4 out of 10, Exceptional, (3 reviews)
"This property was comfortable and convenient and we enjoyed our stay here."
United States
Marty
The price is £108
includes taxes & fees
1 Dec - 2 Dec
Downtown Bridgewater Suite near River and Trails

12. Lakefront Cottage • Private Beach • Lake Views • Pets Stay Free • Kayaks & BBQ

Lakefront Cottage • Private Beach • Lake Views • Pets Stay Free • Kayaks & BBQ
Forties
Lakefront Cottage • Private Beach • Lake Views • Pets Stay Free • Kayaks & BBQ

13. Mermaid's Retreat - Caribou Lake Cottage!

Mermaid's Retreat - Caribou Lake Cottage!
Mahone Bay
9.4 out of 10, Exceptional, (10 reviews)
"Fantastic property, location, and hosts. Will be booking again!"
Canada
Josh
The price is £198
includes taxes & fees
9 Nov - 10 Nov
Mermaid's Retreat - Caribou Lake Cottage!

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

Luxury lakefront dome with private beach, close to nature and town!
Lunenburg
10.0 out of 10, Exceptional, (43 reviews)
"Really clean, beautiful view, perfect place to relax"
Canada
Maxime
The price is £201
includes taxes & fees
9 Nov - 10 Nov
Luxury lakefront dome with private beach, close to nature and town!

15. Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail

Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail
Ingramport
9.8 out of 10, Exceptional, (124 reviews)
"Great location and beautiful spot. Our family of 5 really enjoyed our visit!!"
United States
Victoria W.
The price is £267
includes taxes & fees
9 Nov - 10 Nov
Lovely Lakefront Cottage near Sandy Beaches and Hiking / Biking Trail

16. 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, (22 reviews)
"Great place and location and the owners were very helpful!"
Canada
Judy
The price is £191
includes taxes & fees
13 Nov - 14 Nov
Pet-Friendly Glamping Dome close to Peggy’s Cove!

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

Coastal Studio Suite Steps from the Ocean | pet friendly
Boutiliers Point
The price is £101
includes taxes & fees
9 Nov - 10 Nov
Coastal Studio Suite Steps from the Ocean | pet friendly

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

Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.
Bridgewater
8.6 out of 10, Excellent, (15 reviews)
"Great location for us and very clean and spacious."
Canada
Christina
The price is £168
includes taxes & fees
4 Dec - 5 Dec
Luxurious 2 Bedroom with King and Queen bed and 1.5 Bathroom sleeps 6.

19. Cozy Garden View Suite near Lunenburg Waterfront (Suite 6)

Cozy Garden View Suite near Lunenburg Waterfront (Suite 6)
Lunenburg
9.2 out of 10, Wonderful, (5 reviews)
"Beautiful room … very well done"
Canada
Camil
The price is £182
includes taxes & fees
9 Nov - 10 Nov
Cozy Garden View Suite near Lunenburg Waterfront (Suite 6)

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

Relaxing King Bed Suite Close to Lunenburg Harbour (Suite 2)
Lunenburg
9.4 out of 10, Exceptional, (8 reviews)
"It is a lovely place to stay! Very clean, very inviting."
Canada
Danette R.
The price is £160
includes taxes & fees
9 Nov - 10 Nov
Relaxing King Bed Suite Close to Lunenburg Harbour (Suite 2)
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.

Find holiday rentals that suit your style

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 £101 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?

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort: This holiday 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 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. Chester Art Center 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.

Explore a world of travel with Expedia