Chepstow Holiday Rentals

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Holiday Rentals in Chepstow

Wheelhouse Inn #1
9.4 out of 10, Exceptional, (30)
"This is a lovely, quaint location, near the water and historic properties. The owner was very helpful and kind. The unit was modern and lovely! "
Canada
Julia
The price is AU$207
includes taxes & fees
31 Oct - 1 Nov
Wheelhouse Inn #1
Stunning Guesthouse in historic Georgetown w/hot tub!
9.2 out of 10, Wonderful, (61)
"We stayed at this wonderful home which exceeded our expectations. We enjoyed having a restaurant across the street, strolling along the walkway, ocean view and relaxation in the hot tub. The owner was a great communicator and this place had lots of room with great cleanliness. I highly recommend this place to stay and hope to return to experience more great PEI hospitality. "
Canada
Maureen
The price is AU$374
includes taxes & fees
3 Nov - 4 Nov
Stunning Guesthouse in historic Georgetown w/hot tub!
Chapel Suites - 2 Queen Suite
9.8 out of 10, Exceptional, (57)
"Excellent location and great room! We would stay here again."
Canada
Kathleen G.
The price is AU$237
includes taxes & fees
1 Nov - 2 Nov
Chapel Suites - 2 Queen Suite
Ernie’s paradise where peacefulness is our priority
Ernie’s paradise where peacefulness is our priority
Charming 2-bedroom cottage with AC and WiFi in delightful Saint Peters Bay
9.2 out of 10, Wonderful, (7)
"Great attention to detail and responsive host! This is a great home base for exploring this part of the island!"
Canada
Sarah U.
Charming 2-bedroom cottage with AC and WiFi in delightful Saint Peters Bay
Chapel Suites - King Suite
9.6 out of 10, Exceptional, (52)
"Comfortable bed, towels were nice."
Canada
Donna
The price is AU$237
includes taxes & fees
1 Nov - 2 Nov
Chapel Suites - King Suite
Newly renovated 2 bedroom house with view of the Souris Harbour & marina.
10.0 out of 10, Exceptional, (46)
"A superb VRBO , with First Class Hosts !"
Canada
philip
Newly renovated 2 bedroom house with view of the Souris Harbour & marina.
Lower Loop Country Home/Surrounded by beautiful Canadian beaches!
10.0 out of 10, Exceptional, (1)
"The house was spacious, so that we (five adults) did not get into each others way. It was not lacking anything. The bbq was great, and many small things that made it like home. It is a gem."
Canada
Klaus H.
Lower Loop Country Home/Surrounded by beautiful Canadian beaches!
NEW! Secluded Beachfront Retreat with Luxury Amenities
10.0 out of 10, Exceptional, (7)
"Gorgeous and well maintained property with great beach access. Hosts were a pleasure to interact with. Highly recommend and would return without hesitation. "
Canada
Charles L.
NEW! Secluded Beachfront Retreat with Luxury Amenities
The Summerhouse at St. Peters
10.0 out of 10, Exceptional, (6)
"great cottage right outside of town with a great view of the harbor."
United Kingdom
Mitch L.
The Summerhouse at St. Peters
Beautiful Coastal Beach House. New build close to golf and beaches .
10.0 out of 10, Exceptional, (8)
"This property was great, beautiful view of the bay, very nice interior and finishes. I would recommend to anyone and would stay again! "
Canada
Marc T.
Beautiful Coastal Beach House. New build close to golf and beaches .
Cozy, private ocean/ beach front cottage with spectacular views in Fortune PEI
10.0 out of 10, Exceptional, (58)
"We loved our time here - we really felt like we were away from everything! The kids loved exploring the beach, which was full of shells. I loved looking out at the water. The house was plenty big for our family of 4 as the second bedroom contained 2 beds. I really appreciated the list of area attractions Cathy sent us before we arrived. It really helped us plan out what we would do during our time on the island!"
United States
Lisa K.
Cozy, private ocean/ beach front cottage with spectacular views in Fortune PEI
Beautiful Getaway Plus More!
10.0 out of 10, Exceptional, (24)
"Lovely property. Clean, tidy, cute and very comfortable with a nice open concept. Great deck for lounging."
Canada
Craig E.
Beautiful Getaway Plus More!
Seabreeze Beach Retreat located in scenic Souris, PEI. Family and pet friendly.
10.0 out of 10, Exceptional, (4)
"Wonderful property, had everything we needed for our five day stay. Would highly recommend for anyone visiting the island."
United States
John R P.
Seabreeze Beach Retreat located in scenic Souris, PEI. Family and pet friendly.
Close to Beach and Town of Souris. Quaint cottage with lovely log cabin feel.
9.8 out of 10, Exceptional, (18)
"Very nice quiet and clean house in an easily accessible location"
Canada
Bradley
The price is AU$346
includes taxes & fees
29 Oct - 30 Oct
Close to Beach and Town of Souris. Quaint cottage with lovely log cabin feel.
Breathtaking Views, Absolute Privacy, Modern&Cozy! 5mins to PEI's 2 BEST Beaches
6.0 out of 10, (3)
"We appreciated the view of the ocean and sights of many beautiful birds. The private and quiet setting allowed us to fully relax and enjoy our stay. The swimming pool was a great bonus which we took advantage off. Bothwell beach was stunning and just a short 2 min drive from the cottage. The cottage itself was spacious and was well equipped."
Canada
Aleksandra P.
Breathtaking Views, Absolute Privacy, Modern&Cozy! 5mins to PEI's 2 BEST Beaches
Ned's Landing at Spry Point
4.0 star property
9.2 out of 10, Wonderful, (98)
"Excellent few days staying a Ned's Landing!!!"
Canada
Jeffrey
Ned's Landing at Spry Point
Brand New Costal Water Front Cottage with Stunning Ocean Views
10.0 out of 10, Exceptional, (16)
" An amazing property in every way. We loved our time here. Great views and an easy walk to the water. Gracious hosts."
United States
Leone C.
Brand New Costal Water Front Cottage with Stunning Ocean Views
The Lamplighter Inn at East Point Lighthouse
10.0 out of 10, Exceptional, (1)
"A beautiful property overlooking the lighthouse and the ocean! Beautiful sunrises from wraparound decks with plenty of seating for everyone. The house inside is beautiful too with everything you could ever need. The owners were extremely helpful and responsive and have thought of everything to make your stay comfortable and enjoyable. "
Canada
Carol
The Lamplighter Inn at East Point Lighthouse
Georgetown Oasis near Golf Courses & Provincial Park
9.0 out of 10, Wonderful, (4)
"Great experience!"
Canada
Robert S.
Georgetown Oasis near Golf Courses & Provincial Park
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 Chepstow Hotel Reviews

Find out more about Chepstow

Everything you need to know about Chepstow 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 Chepstow 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 Chepstow holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Chepstow holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chepstow. 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 Chepstow 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 Chepstow holiday rentals we have selected for you start as low as AU$207 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Chepstow rentals

At Expedia, we put the best Chepstow 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 Chepstow 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 Chepstow 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 Chepstow. 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

Can I find a holiday rental in Chepstow?

Yes, there are holiday rentals close to the most popular sights in Chepstow, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Chepstow has to offer?

Stunning Guesthouse in historic Georgetown w/hot tub!: This holiday home rental outside of Chepstow is located by the ocean, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and 1 hot tub.

What can I see and do in Chepstow?

While exploring the area, visit family-friendly sights like Elmira Railway Museum, or get outside and enjoy nature at Basin Head Provincial Park. Souris Lighthouse and Souris Ferry Terminal are a couple of places you'll find in the wider area.

What are holiday rentals like in Chepstow?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Chepstow. Holiday rentals feature amenities such as kitchens and laundry facilities so you'll feel right at home. If you're concerned about cleanliness, holiday rentals can offer a sense of seclusion away from shared hotel lifts and busy lobbies while still allowing you to travel. You'll also have more space in a holiday rental than in a hotel, which makes a holiday rental an attractive choice for family trips.