Holiday Rentals in Chester

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Holiday Rentals in Chester

Private cottage on the ocean with a beautiful view that you’ll love.
Interior
Private cottage on the ocean with a beautiful view that you’ll love.
9.6 out of 10, Exceptional, (4)
"IF you want something private and beautiful this is the place. It is off the beaten path but well worth it. Getting to see deer every day was amazing. You can even roll down your window and talk to the them. It was exactly the peace we needed. The view is breathtaking."
Private cottage on the ocean with a beautiful view that you’ll love.
Idyllic, sparkling clean ocean/beach cottage for your spontaneous getaway.
Outdoor dining
Idyllic, sparkling clean ocean/beach cottage for your spontaneous getaway.
9.8 out of 10, Exceptional, (117)
"Lovely property ,lovely hosts.spectacular views ,all amenities provided close to everything 👍"
Idyllic, sparkling clean ocean/beach cottage for your spontaneous getaway.
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg
Fridge, microwave, oven, stovetop
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg
10.0 out of 10, Exceptional, (59)
"Great weekend with friends. Frank & Val pull out all the stops for their guests. This is by far the best place for anyone with allergies to scented products. The cottage is supplied with everything you need and all scent free. The kitchen is a dream, well-stocked and spacious. The deck and fire pit area were an added bonus. We loved our stay and will visit again."
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg
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Entire house, Bridgewater. 2 Bedrooms, sleeps 4, 1.5 baths
Beach nearby, beach towels
Entire house, Bridgewater. 2 Bedrooms, sleeps 4, 1.5 baths
10.0 out of 10, Exceptional, (66)
"Everything about the property was wonderful - quiet location, exceptionally clean home, lovely decor, very comfortable beds, every amenity needed to enjoy home away. Highly recommend."
Entire house, Bridgewater. 2 Bedrooms, sleeps 4, 1.5 baths
Writer's Retreat: Privacy within sight and sound of the sea
Fridge, microwave, oven, stovetop
Writer's Retreat: Privacy within sight and sound of the sea
9.8 out of 10, Exceptional, (32)
"This was our third time staying at Rosalie's cottage and it was as lovely as ever."
Writer's Retreat: Privacy within sight and sound of the sea
Private Island, Ocean Front, Aspotogan Pennisula, South Shore Nova Scotia
Aerial view
Private Island, Ocean Front, Aspotogan Pennisula, South Shore Nova Scotia
9.8 out of 10, Exceptional, (67)
"Spent a wonderful three days here. Its a gorgeous, remote location to get away from it all!"
Private Island, Ocean Front, Aspotogan Pennisula, South Shore Nova Scotia
On the Beautiful South Shore Near Chester and Hubbards, Ns
Beach
On the Beautiful South Shore Near Chester and Hubbards, Ns
10.0 out of 10, Exceptional, (72)
"If you are considering staying on the South Shore this property is highly recommended. Everything from start to finish was perfect. It is in a beautiful cove with lovely views from the terrace. Perfect for morning coffee or late evening drinks. The house was clean , spacious and well maintained. It was very well equipped with all household items and amenities. We enjoyed day trips to Luneberg, Mahone Bay and Peggy’sCove as well as shorter jaunts to Chester and Hubbards. Communication with the...
On the Beautiful South Shore Near Chester and Hubbards, Ns
Serenity Tiny House Cottage in Chester
Property grounds
Serenity Tiny House Cottage in Chester
10.0 out of 10, Exceptional, (51)
"Sandra and Bill are fantastic hosts, who have built and outfitted this tiny home with such thoughtfulness and intention, that it was very difficult to bid it goodbye. The Southern Shore of Nova Scotia is one of the most beautiful- and friendliest - places I have ever been. Im counting down the days until I can visit next. Or retire here."
Serenity Tiny House Cottage in Chester
Mahone Bay Hide-Away
TV
Mahone Bay Hide-Away
10.0 out of 10, Exceptional, (48)
"Lovely decorate property, very clean and bright. Great location not far from Halifax. Totally recommend this property. Cheers"
Mahone Bay Hide-Away
Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove
Property grounds
Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove
10.0 out of 10, Exceptional, (64)
"Very clean, very well stocked, and nice decor! Highly recommend!"
Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove
One bedroom fully equipped Mahone Bay luxury cottage
Fridge, microwave, oven, stovetop
One bedroom fully equipped Mahone Bay luxury cottage
10.0 out of 10, Exceptional, (69)
"Beautiful cottage. Very clean and everything that we needed was there. Will definitely recommend to our friends!"
One bedroom fully equipped Mahone Bay luxury cottage
Architecturally-designed in Lunenburg - The Bayswater
Beach
Architecturally-designed in Lunenburg - The Bayswater
9.2 out of 10, Wonderful, (10)
"Lovely location, yet parking could be an issue during peak season. Finding parking in the evening was easy though."
Architecturally-designed in Lunenburg - The Bayswater
Beautiful Home on Sunny Acreage w/full bath & nearby ocean
Exterior
Beautiful Home on Sunny Acreage w/full bath & nearby ocean
10.0 out of 10, Exceptional, (2)
"Property was as advertised and expected We stayed two nights, and prepared 3 of our meals on location. The kitchen was clean, and we’ll provided with nice cookware and dishware needed for meal prep and eating in. The host greeted us as we arrived, and gave us helpful comments about the ac/heat, the tv, and property. In retrospect as most in their 40s and older are not as intuitive as millennials and genders, it would be helpful to have a simple instruction outline on the tv and ac/heat. On our...
The price is €191
per night
4 May - 5 May
Beautiful Home on Sunny Acreage w/full bath & nearby ocean
On a quiet, narrow Lane walking distance to all amenities
Property grounds
On a quiet, narrow Lane walking distance to all amenities
10.0 out of 10, Exceptional, (80)
"Charming great little cottage fully equipped right down to a clothes line if you don’t wish to use the dryer, bbq and lovely back deck. Having 2 bathrooms was a bonus. Walking distance to stores, restaurants, etc all within 10 minutes. Excellent base to south shore destination- an hour to Halifax. Would book this one again in a heartbeat!"
On a quiet, narrow Lane walking distance to all amenities
Spectacular Oceanfront Living in Authentic Fishing Village
Terrace/patio
Spectacular Oceanfront Living in Authentic Fishing Village
10.0 out of 10, Exceptional, (88)
"Great space lots of room! Host always available"
Spectacular Oceanfront Living in Authentic Fishing Village
RYA - 2023 - 24 - 03281153042804049 - 20<br>House with four bedrooms and deck
Property grounds
RYA - 2023 - 24 - 03281153042804049 - 20<br>House with four bedrooms and deck
6.0 out of 10, (2)
"We enjoyed our stay close to local beaches, kayak/paddle board rentals and in between Halifax and Mahone Bay. The owner was very attentive and thoughtful of our needs. We were welcomed with a bottle of wine and the owner brought family videos and yummy coffee for us. It was well equipped with a wonderful washer dryer, BBQ, waffle maker and coffee maker as well as many items for guests. The deck was handy to enjoy meals and watch the deer in the morning and water throughout the day and evening. I...
RYA - 2023 - 24 - 03281153042804049 - 20<br>House with four bedrooms and deck
The Nest at Deep Cove
Pool
The Nest at Deep Cove
10.0 out of 10, Exceptional, (19)
"The property is in a beautiful location, and very well equipped. We enjoyed the solitude and view. It was a great place for the 30ish family that joined us. There were lots of trails that they used for hiking and running. Alan even supplied us with firewood, which we used. We would certainly consider revisiting! The few questions we texted were answered immediately. Great property and management."
The Nest at Deep Cove
Knotting Hill - A charming maritime century home
Property grounds
Knotting Hill - A charming maritime century home
Knotting Hill - A charming maritime century home
Beautiful Lakefront Cottage
Property grounds
Beautiful Lakefront Cottage
10.0 out of 10, Exceptional, (23)
"It was a perfect location for day trips and hang around relaxation. The serenity and sunsets were amazing. Nancy was certainly a premier hostess. Highly recommend! ."
Beautiful Lakefront Cottage
One bedroom fully equipped Mahone Bay luxury cottage
Fridge, microwave, oven, stovetop
One bedroom fully equipped Mahone Bay luxury cottage
10.0 out of 10, Exceptional, (29)
"Exactly as depicted and divine."
One bedroom fully equipped Mahone Bay luxury cottage
Don't see what you're looking for?
See all available properties in Chester
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.

Other types of properties in Chester you may be interested in

Best Western Plus Bridgewater Hotel & Convention Centre
Indoor pool
Best Western Plus Bridgewater Hotel & Convention Centre
3.5 star property
9.2 out of 10, Wonderful, (734)
"The hotel is clean…we were warned about renovations closing the restaurant which was fine…but they didn’t mention that nail guns would be starting at 7 am :( We also were disappointed that housekeeping skipped our room…4 day stay, leaving by 9 in morning and each night we returned to dirty towels…Also pool was too cold…no hot tub…"
The price is €131
per night
20 May - 21 May
Best Western Plus Bridgewater Hotel & Convention Centre
Smugglers Cove Inn
City view from property
Smugglers Cove Inn
4.0 star property
9.0 out of 10, Wonderful, (488)
" Very well positioned for the waterfront and restaurants. Kind and helpful management and staff."
The price is €123
per night
11 May - 12 May
Smugglers Cove Inn
Days Inn & Conference Center by Wyndham Bridgewater
Suite, 1 King Bed, Non Smoking (One-Bedroom)
Days Inn & Conference Center by Wyndham Bridgewater
2.5 star property
7.4 out of 10, Good, (959)
"I was very pleased with how I was treated and the clean areas of the building."
The price is €118
per night
4 May - 5 May
Days Inn & Conference Center by Wyndham Bridgewater
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.

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 €191 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?

Private Island, Ocean Front, Aspotogan Pennisula, South Shore Nova Scotia: This holiday home rental outside of Chester is located on the beach, and has a fireplace, a patio and laundry facilities to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a fridge, a stovetop and a microwave, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of books.

How many holiday rentals will I find in Chester?

Choose from 13 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.

Recent reviews of Chester properties
Expedia verified reviews

Smugglers Cove Inn

Smugglers Cove Inn

5/5 Excellent
Very well situated.
" Very well positioned for the waterfront and restaurants. Kind and helpful management and staff."
A verified traveller stayed at Smugglers Cove Inn
Posted 2 days ago
Smugglers Cove Inn