Chester Race Week
Where to stay for Chester Race Week.
Racing runs August 11 to 14, 2027, and the organizers advise booking early, because rooms fill up fast in race week. 2 Casa Scotia homes are in Chester Basin, 10 and 16 minutes’ drive from the Chester Yacht Club, and 3 more are on St. Margarets Bay. They’re whole houses, and they sleep 6 to 10.
Search every Casa Scotia home for August 10 to 15, 2027: the night before the first race to the morning after the last.
Homes near Chester, nearest first
5 homes. Tap one for its dates and prices.
The Oaks Seaside Retreat
Chester Basin · South Shore
10 min drive to the Chester Yacht Club
Sleeps 10 · 5 bedrooms
Waterfront with a private dock and hot tub
See dates & prices
Spyglass Seastead
Chester Basin · South Shore
16 min drive to the Chester Yacht Club
Sleeps 8 · 4 bedrooms
Circa-1890 farmhouse near Oak Island
NS registration STR2627D0280
See dates & prices
Oceanfront Sanctuary
Hubbards · St. Margarets Bay
34 min drive to the Chester Yacht Club
Sleeps 8 · 4 bedrooms
Private oceanfront with a hot tub and sauna
NS registration STR2627B8450
See dates & prices
Oceanfront Home with Private Water Access
Head of St. Margarets Bay
35 min drive to the Chester Yacht Club
Sleeps 8 · 4 bedrooms
Oceanfront with private water access
NS registration STR2627B3076
See dates & prices
Sea House at Whynachts Cove
Tantallon · St. Margarets Bay
40 min drive to the Chester Yacht Club
Sleeps 6 · 3 bedrooms
Waterfront on Whynachts Cove
NS registration STR2627B2576
See dates & pricesDriving times run from each home to the Chester Yacht Club, 21 South Street, by road and without traffic. Each home’s booking page has its live calendar, prices and house rules.
Homes at a glance
Tap a home to see its live calendar and prices.
| Home | Town | Drive to the yacht club | Sleeps | Bedrooms | Registration |
|---|---|---|---|---|---|
| The Oaks Seaside Retreat | Chester Basin | 10 min | 10 | 5 | |
| Spyglass Seastead | Chester Basin | 16 min | 8 | 4 | STR2627D0280 |
| Oceanfront Sanctuary | Hubbards | 34 min | 8 | 4 | STR2627B8450 |
| Oceanfront Home with Private Water Access | Head of St. Margarets Bay | 35 min | 8 | 4 | STR2627B3076 |
| Sea House at Whynachts Cove | Tantallon | 40 min | 6 | 3 | STR2627B2576 |
Swipe the table sideways to see every column.
Planning a Race Week stay
When is Chester Race Week 2027?
August 11 to 14, 2027, by the race’s own calendar; in 2028 it’s August 16 to 19. Billed as Canada’s largest keelboat regatta, it’s four days of racing on Mahone Bay off Chester, run from the Chester Yacht Club, with live music, food trucks and parties ashore. Schedules and entries are on chesterraceweek.com.
Which homes are closest to the Chester Yacht Club?
The Oaks Seaside Retreat in Chester Basin, about 10 minutes’ drive, and Spyglass Seastead, also in Chester Basin, about 16. On St. Margarets Bay, Oceanfront Sanctuary in Hubbards is about 34 minutes away, the Oceanfront Home with Private Water Access at the head of the bay about 35, and the Sea House at Whynachts Cove in Tantallon about 40.
Can a whole crew stay in one house?
Yes. Each is a whole house, and they sleep 6 to 10. The Oaks Seaside Retreat sleeps 10 in a main house and a carriage house on the water. Bringing more people than one house holds? See group stays or call us at (902) 707-0329.
How early should we book?
As early as you can: the organizers advise booking early, because rooms fill up fast in race week. The link at the top of this page searches every Casa Scotia home for August 10 to 15, 2027; the homes listed here are the ones near Chester.
Where can we moor a boat?
The race’s own accommodations and moorage page lists the options: the Chester Yacht Club has moorings for boats registered in the race, and marinas around Chester offer more.
More ways to stay
Pick your dates. The rest is handled.
Live availability and prices on our booking site — never priced above the platforms before tax.