Oak Island Tours

If your idea of a fantastic vacation means being near the water, make a beeline for Oak Island. Whatever you choose to do here, you're unlikely to tire of those lovely views.

Located in Chester, this water-surrounded land mass is often on the itineraries of many travelers. Appealing attractions, such as Chester Golf Club, are nearby if you're up for some exploring.

Plan a trip to see Oak Island

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express & Suites Halifax Airport by IHG

Holiday Inn Express & Suites Halifax Airport by IHG

2.5 out of 5
Price was $670, price is now $529 per person
$529
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
8.8/10 Excellent! (2,179 reviews)
It was a convenient place to stay in between flight and final destination of Nova Scotia. The shuttle service was not reliable and not what it stated to be running every 30 minutes.

Reviewed on Sep 2, 2025

Lux Exec Home HFX Waterfront Pool Hot Tub

Lux Exec Home HFX Waterfront Pool Hot Tub

4.5 out of 5
Save 100% on your flight
Price was $1,798, price is now $1,067 per person
$1,067
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
10/10 Exceptional! (4 reviews)
Our stay was fabulous! The ho

Reviewed on Jul 25, 2025

Nalu Retreat & Nordic Spa

Nalu Retreat & Nordic Spa

5 out of 5
Price was $1,339, price is now $1,073 per person
$1,073
per person
Nov 7 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Halifax (YHZ)
9.6/10 Exceptional! (24 reviews)
Sandi was very helpful … beautiful views.. bucket list experience !!!! 10/10

Reviewed on Jul 7, 2025

Popular places to visit

Valverde Studio Gallery

You can spend time exploring the galleries in Valverde Studio Gallery during your trip to Chester. Stroll along this family-friendly area's waterfront, or simply enjoy its seafood restaurants.

Valverde Studio Gallery

Tancook Island

Find out about the history of Chester with a stop at Tancook Island. While in this family-friendly area, you can savor the top-notch restaurants.

Tancook Island

Chester Playhouse

You can enjoy a show at Chester Playhouse during your trip to Chester. Stroll along this family-friendly area's waterfront, or simply enjoy its seafood restaurants.

Chester Playhouse

Amicus Gallery

You can spend time studying the exhibits at Amicus Gallery in Chester. Stroll along this family-friendly area's waterfront, or simply enjoy its seafood restaurants.

Amicus Gallery

Lordly House Museum

You can spend time studying the exhibits at Lordly House Museum during your trip to Chester. While in this family-friendly area, you can savor the top-notch restaurants.

Lordly House Museum

Chester Art Center

You can spend an afternoon browsing the exhibits at Chester Art Center during your trip to Chester. Stroll along this family-friendly area's waterfront, or simply enjoy its seafood restaurants.

Chester Art Center

Best Lodging Options Near Oak Island

Oceanfront Luxury Magical Views Sunset and Sunrise

Oceanfront Luxury Magical Views Sunset and Sunrise

Western Shore
Oceanfront Luxury Magical Views Sunset and Sunrise
Oak Island Resort & Conference Centre

Oak Island Resort & Conference Centre

3.5 out of 5
36 Treasure Drive, Western Shore, NS
Oak Island Resort & Conference Centre
Miller House By the Bay

Miller House By the Bay

2 out of 5
624 Main street, mahone bay, NS
Miller House By the Bay
Fairmont House Bed & Breakfast

Fairmont House Bed & Breakfast

3 out of 5
654 Main Street, Mahone Bay, NS
Fairmont House Bed & Breakfast
Black Forest Cabins

Black Forest Cabins

3 out of 5
15 Longhill Rd, Mahone Bay, NS
Black Forest Cabins
Magnolia Inn

Magnolia Inn

4.5 out of 5
610 Main St, Mahone Bay, NS
Magnolia Inn
One bedroom fully equipped Mahone Bay luxury cottage

One bedroom fully equipped Mahone Bay luxury cottage

Mahone Bay
One bedroom fully equipped Mahone Bay luxury cottage
Mahone Bay Town Center 2 Bedroom Apt. - Steps to Everything - Vacation Oasis

Mahone Bay Town Center 2 Bedroom Apt. - Steps to Everything - Vacation Oasis

Mahone Bay
Mahone Bay Town Center 2 Bedroom Apt. - Steps to Everything - Vacation Oasis
Mahone Bay Hide-Away

Mahone Bay Hide-Away

Mahone Bay
Mahone Bay Hide-Away
See all 391 properties in Oak Island
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.