Chester Holiday Rentals

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Holiday Rentals in Chester

Smart TV, fireplace, ping pong, books
1800' | Front HBR | DT 5 Min Walk | Water views
10.0 out of 10, Exceptional, (1)
"Great location and easy access to restaurants, shops. Bed was quite comfortable."
1800' | Front HBR | DT 5 Min Walk | Water views
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
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.
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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
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 NZ$329
per night
17 May - 18 May
Beautiful Home on Sunny Acreage w/full bath & nearby ocean
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
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
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
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.
TV
Mahone Bay Hide-Away
10.0 out of 10, Exceptional, (49)
"Lovely decorate property, very clean and bright. Great location not far from Halifax. Totally recommend this property. Cheers"
Mahone Bay Hide-Away
Property grounds
Oceanfront 2BR Private Apartment
9.8 out of 10, Exceptional, (46)
"Beautiful location, terrific host, very comfortable"
Oceanfront 2BR Private Apartment
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
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
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
Property grounds
"Lisette's on Long Hill", cozy with boho charm
9.4 out of 10, Exceptional, (9)
"the fire pit"
"Lisette's on Long Hill", cozy with boho charm
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
Property grounds
Rock Haven Cottage, on the ocean!
10.0 out of 10, Exceptional, (65)
"The cottage was perfect for my family's stay. The place was well-designed, clean, and comfortable. I would recommend staying here to anyone looking for a quiet getaway."
Rock Haven Cottage, on the ocean!
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
Property grounds
Knotting Hill - A charming maritime century home
Knotting Hill - A charming maritime century home
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
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

Smart TV, fireplace, ping pong, books
1800' | Front HBR | DT 5 Min Walk | Water views
10.0 out of 10, Exceptional, (1)
"Great location and easy access to restaurants, shops. Bed was quite comfortable."
1800' | Front HBR | DT 5 Min Walk | Water views
Indoor pool
Best Western Plus Bridgewater Hotel & Convention Centre
3.5 star property
9.2 out of 10, Wonderful, (739)
"Under construction, so breakfast was lacking. "
The price is NZ$231
per night
24 May - 25 May
Best Western Plus Bridgewater Hotel & Convention Centre
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 NZ$259
per night
21 May - 22 May
Smugglers Cove Inn
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Chester holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Chester. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Chester. Seeing all the best attractions is bound to make you fall in love with Chester. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Chester short-term rentals, that won’t be hard to do.

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