Chester Holiday Rentals

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Holiday Rentals in Chester

Black Forest Cabins

3.0 star property
Mahone Bay
10.0 out of 10, Exceptional, (19)
"Bed was very comfortable,and clean and spacious. Everything I needed was there and close to trails and the downtown."
Canada
Mary
The price is AU$265
includes taxes & fees
9 Dec - 10 Dec
Black Forest Cabins

Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove

Indian Harbour
10.0 out of 10, Exceptional, (89)
"A great place to stay. Very clean and cozy. Decorated very tastefully. Local Acadian restaurant was perfect. Would love to go back again."
Canada
Floyd
Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove

One bedroom fully equipped Mahone Bay luxury cottage

Mahone Bay
10.0 out of 10, Exceptional, (104)
"Fantastic hosts and wonderful accommodation! "
Canada
Karen D.
One bedroom fully equipped Mahone Bay luxury cottage

Mahone Bay Hide-Away

Mahone Bay
10.0 out of 10, Exceptional, (95)
"Great weekend getaway for us. Clean, comfortable with more amenities than we could use during our stay. Great host met us the first day and answered our questions and gave advice on dining out. "
Canada
Douglas M.
Mahone Bay Hide-Away

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

Ingramport
9.8 out of 10, Exceptional, (221)
"Lots of amenities. Owners very helpful in recommending local restaurants. Enjoyed finding mussels and sea glass on the little beach as well as the antics of the "rock" beavers. The heated pool was a plus. Absolutely wonderful views of the bay."
United States
Jo L.
The Land Yacht – Indoor Pool, Hot Tub, Solarium Lounge & Sublime Ocean Views

Spruce Bell Tent near Peggy's Cove

East Dover
7.6 out of 10, Good, (4)
"I loved it there, it was quite peaceful. I would have loved a coffee pot or some dishes, maybe a microwave and no cost for propane considering it was a tent and it was 200.oo plus dollars per night. Other than that is was great "
Canada
Dana R.
Spruce Bell Tent near Peggy's Cove

Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia

Hubbards
10.0 out of 10, Exceptional, (98)
"A beautiful spot, peaceful and relaxing, Wonderful hosts and lovely accommodation "
Canada
Kathleen M.
Private Island, Ocean Front, Aspotogan Peninsula, South Shore Nova Scotia

Remodelled historic suite w/nautical boho decor, in the UNESCO Town of Lunenburg

Lunenburg
9.8 out of 10, Exceptional, (16)
"Our stay was perfect! The space had everything we needed and more. Great welcoming hosts and a nice clean place. Highly recommend! "
Canada
Karen T.
Remodelled historic suite w/nautical boho decor, in the UNESCO Town of Lunenburg

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

Lunenburg
9.0 out of 10, Wonderful, (7)
"Close to town , clean and comfortable "
United States
Tom D.
The price is AU$276
includes taxes & fees
9 Dec - 10 Dec
Romantic Getaway w/ King Bed in Historic Lunenburg (Suite 4)

Oceanfront 2BR Private Apartment

Head of Saint Margarets Bay
9.8 out of 10, Exceptional, (74)
"We had a lovely stay, the apartment was perfect. "
Canada
Randy
Oceanfront 2BR Private Apartment

Rock Haven Cottage, on the ocean!

McGraths Cove
10.0 out of 10, Exceptional, (95)
"this was our 2nd year to stay at rock haven and probably not our last. the cottage supplied every thing we needed and the location , dock, kayaks and locals provided great entertainment for our stay"
Canada
susan m.
Rock Haven Cottage, on the ocean!

Wilson's Coastal Club - C3

Boutiliers Point
9.8 out of 10, Exceptional, (8)
"Nice place, close to the water with a small private beach"
United States
Tim D.
The price is AU$177
includes taxes & fees
10 Dec - 11 Dec
Wilson's Coastal Club - C3

Moonlight Cottage

Hubbards
9.2 out of 10, Wonderful, (20)
"Perfect vacation, location "
Canada
manon l.
Moonlight Cottage

Beach Front Oasis - Custom-built Timber Frame Home on Cleveland Beach 12 guests

Hubbards
9.6 out of 10, Exceptional, (15)
"Wonderful house with ample room "
Canada
Nadine N.
Beach Front Oasis - Custom-built Timber Frame Home on Cleveland Beach 12 guests

Red Roof Bed & Breakfast

Lunenburg
9.6 out of 10, Exceptional, (9)
"A lovely little cottage, with the added bonus of a gift shop filled with curious trinkets! Would definitely stay here again if I’m ever back in Lunenberg."
Canada
Raeleen
The price is AU$300
includes taxes & fees
9 Dec - 10 Dec
Red Roof Bed & Breakfast

Wilson's Coastal Club - C7

Boutiliers Point
9.6 out of 10, Exceptional, (10)
"Accommodation was excellent, particularly the hot tub overlooking the bay. "
Canada
David B.
The price is AU$244
includes taxes & fees
9 Dec - 10 Dec
Wilson's Coastal Club - C7

Amazing ocean view/ private road/close to bayswater beach.

Hubbards
8.6 out of 10, Excellent, (49)
"Great property for a quiet get away"
Canada
Debora
Amazing ocean view/ private road/close to bayswater beach.

Ocean front cottage, relax and enjoy the sunset over St. Margaret's Bay!

Hacketts Cove
10.0 out of 10, Exceptional, (38)
"This place is amazing and feels like home. It’s extremely clean. Beth is super nice and made us feel so welcomed. I highly recommend this place. "
United States
Yuxin
Ocean front cottage, relax and enjoy the sunset over St. Margaret's Bay!

Oceanfront 3 Bedroom Cottage 5 Minutes from Peggy's Cove.

Hacketts Cove
9.6 out of 10, Exceptional, (53)
"Beautiful house, great location"
United States
Carolyn A.
Oceanfront 3 Bedroom Cottage 5 Minutes from Peggy's Cove.

Cozy Ocean Front Cottage

Lunenburg
9.4 out of 10, Exceptional, (6)
"We had a wonderful 4-night stay at this property while visiting our son, who is working as a deckhand on the Bluenose II in nearby Lunenburg, NS. The cottage was the perfect home base for our trip, offering a comfortable and relaxing place to return to each day.Our host was incredibly welcoming and thoughtful, ensuring we had everything we needed for a great visit. The property itself was immaculate, and the location was ideal for exploring the area. We highly recommend this cottage to anyone...
Canada
Craig A.
Cozy Ocean Front Cottage
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, 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 favourite 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 depend 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 AU$177 per night. Entering your travel dates in the search wizard might find you 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?

Mahone Bay Hide-Away : This holiday home rental outside of Chester offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Chester?

Choose from 14 Expedia holiday rentals in Chester for a memorable holiday.

What’s there to see and do in Chester?

Cultural attractions to visit include Lordly House Museum and Chester Playhouse. 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.