Chester Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Oct 17 - Oct 19
In one month
Oct 31 - Nov 2
In two months
Nov 28 - Nov 30
In three months
Dec 26 - Dec 28

Vacation Rentals in Chester

Family Home In the Heart of the Village of Chester
Terrace/patio

Family Home In the Heart of the Village of Chester

9.6 out of 10, Exceptional, (28)
"Spacious, clean, comfortable, and lots of room for people to spread out. We would happily return."
Family Home In the Heart of the Village of Chester
Oakhill Pines Campground
Cabin, Multiple Beds, Shared Bathroom | Desk, free WiFi

Oakhill Pines Campground

3.0 star property
8.8 out of 10, Excellent, (15)
"Great place"
Oakhill Pines Campground
Black Forest Cabins
Meeting facility

Black Forest Cabins

3.0 star property
10.0 out of 10, Exceptional, (9)
"Great spot for a special night out … beds were super comfortable "
The price is ￥30,720
￥38,674 total
includes taxes & fees
Oct 14 - Oct 15
Black Forest Cabins
Juniper Bell Tent near Peggy's Cove
Property grounds

Juniper Bell Tent near Peggy's Cove

8.8 out of 10, Excellent, (3)
"Good for a nights stay and close to Peggy’s cove. Comfy and enough space"
The price is ￥12,816
￥21,593 total
includes taxes & fees
Oct 1 - Oct 2
Juniper Bell Tent near Peggy's Cove
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg
Full-size fridge, microwave, oven, stovetop

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

10.0 out of 10, Exceptional, (110)
"I wish we had more time to enjoy the cottage. There was so much to see in area, we were busy all day, but a comfy place to come home too. "
Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg
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, (101)
"Great cottage to use as a base to discover the area. Well equipped, quiet and close to restaurants and shopping."
The price is ￥16,093
￥29,353 total
includes taxes & fees
Oct 13 - Oct 14
One bedroom fully equipped Mahone Bay luxury cottage
Oceanfront 3-Bedroom Captain's House
Dining

Oceanfront 3-Bedroom Captain's House

9.8 out of 10, Exceptional, (27)
"Perfect house, perfect location, fabulous area to vacation!"
Oceanfront 3-Bedroom Captain's House
Whalesback Cottage, on the ocean with access to Peggys Cove Preservation Area
Interior

Whalesback Cottage, on the ocean with access to Peggys Cove Preservation Area

9.8 out of 10, Exceptional, (123)
"Cozy cottage with wonderful views. "
Whalesback Cottage, on the ocean with access to Peggys Cove Preservation Area
Pebble Oceanside RV Retreat – Waterfront Hot Tub & Deck
Outdoor dining

Pebble Oceanside RV Retreat – Waterfront Hot Tub & Deck

10.0 out of 10, Exceptional, (3)
"Beautiful location on the water, super friendly hosts. Location close to so many little towns with great food and amazing people. Trailer has everything that you need for your stay, they thought of everything. They made us feel welcome and we will be back for sure. We took our paddleboards out; he even lent us a fishing rod to use on the nearby Warf. "
Pebble Oceanside RV Retreat – Waterfront Hot Tub & Deck
Wilson's Coastal Club - C3
Sauna

Wilson's Coastal Club - C3

10.0 out of 10, Exceptional, (6)
"Nice place, close to the water with a small private beach"
The price is ￥19,128
￥25,868 total
includes taxes & fees
Oct 5 - Oct 6
Wilson's Coastal Club - C3
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring
Terrace/patio

Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring

9.6 out of 10, Exceptional, (34)
"Beautiful setting, very peaceful with lovely linens on the beds. The kitchen is fully stocked, the sitting room is comfortable and the outside decks are amazing. The little village of Chester was close by with a cozy pub offering live music on select nights and the local playhouse had local talent performing while we were there. We would stay again"
Oceanfront Garden Cottage - Gateway to Attractions & Towns. Private Cove Mooring
Ocean front cottage, relax and enjoy the sunset over St. Margaret's Bay!
Dining

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

10.0 out of 10, Exceptional, (34)
"Very nice spot. property nicely decorated and conveniet"
Ocean front cottage, relax and enjoy the sunset over St. Margaret's Bay!
The Land Yacht – Indoor Pool, Hot Tub, Solarium Lounge & Sublime Ocean Views
Interior

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

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."
The Land Yacht – Indoor Pool, Hot Tub, Solarium Lounge & Sublime Ocean Views
Mahone Bay Hide-Away
TV

Mahone Bay Hide-Away

10.0 out of 10, Exceptional, (89)
"Loved this property. So cute and so very clean! Beautifully decorated and very well appointed. Walkable to great restaurants and coffee shops. Loved Mahone Bay and hope to be back. Will definitely stay at this wonderful cottage. "
Mahone Bay Hide-Away
Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove
Terrace/patio

Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove

10.0 out of 10, Exceptional, (85)
"Everything about our trip and this property was amazing. The location, the peace, the scenery, etc. exceeded our expectations. The house was perfect and so comfortable. We hope to be back soon! "
Oceanside Cottage, Spectacular Sunsets, near Peggy's Cove
Unique Ocean View Hilltop Retreat
Exterior

Unique Ocean View Hilltop Retreat

10.0 out of 10, Exceptional, (174)
"Great house with tonnes of character, the hosts answered all questions we had and had good communication!"
Unique Ocean View Hilltop Retreat
Moonlight Cottage
Exterior

Moonlight Cottage

9.2 out of 10, Wonderful, (14)
"Great time, went Peggy’s cove, Hubbard farm market, lunenburg and mahone bay"
Moonlight Cottage
Lunenburg's Cupcake House
Exterior

Lunenburg's Cupcake House

10.0 out of 10, Exceptional, (2)
"What can I say? Lovely hosts, gorgeous cozy property, comfy beds, well-equipped kitchen, thoughtful information pack, board games in the cupboard, everything spotless, and in a great location within a few minutes walk of Lunenberg’s waterfront, shops and restaurants. Even the flowers at the front were in full bloom and smelled amazing! We toured Canada for 5 weeks, as a family of 4, staying in 14 different locations, and this house was my favourite. Thank you so much for a lovely stay! I only...
Lunenburg's Cupcake House
Oceanfront Luxury Magical Views Sunset and Sunrise
2 bedrooms, desk, WiFi, bed sheets

Oceanfront Luxury Magical Views Sunset and Sunrise

9.6 out of 10, Exceptional, (18)
"Short stay, unfortunately, but I’ll definitely be back. "
Oceanfront Luxury Magical Views Sunset and Sunrise
Apple Orchard Cottage Lunenburg, Nova Scotia, Canada
Exterior

Apple Orchard Cottage Lunenburg, Nova Scotia, Canada

9.2 out of 10, Wonderful, (71)
"Older property with character. A bit quirky. Comfy beds and nice sheets etc. Good parking. Very clean. Modern appliances. Couldn't see how to access the 'beach'. A bit of TLC ..Fly screens, windows, doors could do with repair. Toilet flush flap not closing every time"
Apple Orchard Cottage Lunenburg, Nova Scotia, Canada
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

The Homeport Motel

The Homeport Motel

10/10 Excellent
"We loved our stay. Very welcoming and we saw a moose in the surrounding property. "
Joan 1-night trip
Posted 5 days ago
The Homeport Motel

Find out more about Chester

Find out more about Chester

Search for holiday rentals in Chester on Expedia! You can easily find your home rentals, villas, holiday apartments in Chester using one of the methods below:

  • View our selection of featured holiday rentals in Chester
  • Use the map to find apartments and other holiday homes in the Chester neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Chester while they last

Look no further and take a look at our great range of rental properties in Chester!

Frequently asked questions

Are there vacation rentals in Chester?

Yes, there are vacation rentals close to the most popular sights in Chester, or you can choose a secluded option if you'd like a relaxing place to stay. Chester is known for its golf courses and theaters. Make sure you have time to check out the entertainment choices and art during your trip.

What are some of the best vacation rentals in Chester?

4 bed ,2 bathroom home. 2 of the 4 bedrooms are slightly smaller . Still comfort: This vacation home rental outside of 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games.

How many vacation rentals will I find in Chester?

Choose from 13 Expedia vacation rentals in Chester for a memorable vacation.

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 vacation rental in Chester like?

Vacation rentals are privately owned properties you can stay in for short or long periods in Chester. Vacation rentals offer amenities such as hot tubs, fire pits, and patios so you'll feel right at home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of seclusion away from public hotel elevators and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular option for a family trip or a small group gathering.