Book Holiday Homes in Chepstow

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Chepstow

Stunning Guesthouse in historic Georgetown w/hot tub!

Stunning Guesthouse in historic Georgetown w/hot tub!

Georgetown
The price is AU$417 per night from 6 Apr to 7 Apr
AU$417
includes taxes & fees
6 Apr - 7 Apr
When you stay at this vacation home in Georgetown, you'll be on the waterfront, within a 10-minute walk of King's Playhouse and AA MacDonald Memorial ...
Stunning Guesthouse in historic Georgetown w/hot tub!
Beautiful Old Home by the Beach

Beautiful Old Home by the Beach

Georgetown
With a stay at this vacation home in Georgetown, you'll be within a 10-minute walk of King's Playhouse and AA MacDonald Memorial Gardens.
Beautiful Old Home by the Beach
Newly renovated 2 bedroom house with view of the Souris Harbour & marina.

Newly renovated 2 bedroom house with view of the Souris Harbour & marina.

Souris
With a stay at this vacation home in Souris, you'll be on the waterfront, just a 4-minute walk from Souris Visitor Information Centre and 10 minutes by foot ...
Newly renovated 2 bedroom house with view of the Souris Harbour & marina.
Save an average of 15% on thousands of hotels when you're signed in
Seabreeze Beach Retreat located in scenic Souris, PEI.  Family and pet friendly.

Seabreeze Beach Retreat located in scenic Souris, PEI. Family and pet friendly.

Souris
Located in Souris West, this vacation home is a 4-minute drive from Souris Visitor Information Centre and 7 minutes from Souris Lighthouse.
Seabreeze Beach Retreat located in scenic Souris, PEI. Family and pet friendly.
Hare Hideaway with Fireplace

Hare Hideaway with Fireplace

Prince Edward Island
Located in Rollo Bay, this vacation home is by the sea, within a 5-minute drive of The Myriad View Artisan Distillery and Rollo Bay Greens.
Hare Hideaway with Fireplace
The Lamplighter Inn at East Point Lighthouse

The Lamplighter Inn at East Point Lighthouse

Elmira
Located in East Point, this vacation home is on the waterfront, within a 15-minute drive of East Point Lighthouse and Elmira Railway Museum.
The Lamplighter Inn at East Point Lighthouse
Chapel Suites - Deluxe King Suite

Chapel Suites - Deluxe King Suite

Souris
The price is AU$284 per night from 13 Apr to 14 Apr
AU$284
includes taxes & fees
13 Apr - 14 Apr
With a stay at this vacation home in Souris, you'll be within a 5-minute drive of Souris Visitor Information Centre and Souris Lighthouse.
Chapel Suites - Deluxe King Suite
Georgetown Oasis near Golf Courses & Provincial Park

Georgetown Oasis near Golf Courses & Provincial Park

Prince Edward Island
With a stay at this vacation home in Georgetown Royalty, you'll be within a 5-minute drive of AA MacDonald Memorial Gardens and King's Playhouse.
Georgetown Oasis near Golf Courses & Provincial Park
Golfer's Haven!  3-bdrm cottage with modern comforts in a quaint fishing village

Golfer's Haven! 3-bdrm cottage with modern comforts in a quaint fishing village

Georgetown
With a stay at this vacation home in Georgetown, you'll be within a 5-minute walk of AA MacDonald Memorial Gardens and King's Playhouse.
Golfer's Haven! 3-bdrm cottage with modern comforts in a quaint fishing village
Don't see what you're looking for?
See all available properties in Chepstow
View all properties
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.

Chepstow Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Chepstow vacation homes are the perfect way for you to wing it.

Holiday houses in Chepstow let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Chepstow in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Chepstow adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Chepstow with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Chepstow vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Chepstow Holiday Homes essential information

Accommodation
34 Holiday Homes
Lowest Price
AU$245
Highest Price
AU$417
Popular accommodation
Stunning Guesthouse in historic Georgetown w/hot tub!, Beautiful Old Home by the Beach, Newly renovated 2 bedroom house with view of the Souris Harbour & marina., Seabreeze Beach Retreat located in scenic Souris, PEI. Family and pet friendly., Hare Hideaway with Fireplace, The Lamplighter Inn at East Point Lighthouse, Chapel Suites - Deluxe King Suite , Georgetown Oasis near Golf Courses & Provincial Park, Golfer's Haven! 3-bdrm cottage with modern comforts in a quaint fishing village

Top trending hotels in Chepstow

Charming PEI farmhouse with beach access

Charming PEI farmhouse with beach access

Souris
Located in Chepstow, this vacation home is by the sea, within a 5-minute drive of Souris Visitor Information Centre and Souris Lighthouse.
Charming PEI farmhouse with beach access
Stunning Guesthouse in historic Georgetown w/hot tub!

Stunning Guesthouse in historic Georgetown w/hot tub!

Georgetown
The price is AU$417 per night from 6 Apr to 7 Apr
AU$417
includes taxes & fees
6 Apr - 7 Apr
When you stay at this vacation home in Georgetown, you'll be on the waterfront, within a 10-minute walk of King's Playhouse and AA MacDonald Memorial ...
Stunning Guesthouse in historic Georgetown w/hot tub!
Johnson Shore Inn

Johnson Shore Inn

3 out of 5
9984 Northside Road, Route 16, Rock Barra, PE
The price is AU$245 per night from 1 May to 2 May
AU$245
includes taxes & fees
1 May - 2 May
With a stay at Johnson Shore Inn in Rock Barra, you'll be 8.9 mi (14.2 km) from Souris Visitor Information Centre and 9.5 mi (15.3 km) from Souris Ferry ...
Johnson Shore Inn
Save an average of 15% on thousands of hotels when you're signed in
Chapel Suites - 2 Queen Suite

Chapel Suites - 2 Queen Suite

Souris
The price is AU$246 per night from 16 Apr to 17 Apr
AU$246
includes taxes & fees
16 Apr - 17 Apr
Located in Souris, this aparthotel is within a 5-minute drive of Souris Visitor Information Centre and Souris Lighthouse.
Chapel Suites - 2 Queen Suite
Don't see what you're looking for?
See all available properties in Chepstow
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.