The Oaks Seaside Retreat

See all properties

Entire home

Surrounded in pristine landscpaing and gardens

Overview
Amenities
Policies
Location
Host

Exceptional

5 bedrooms5 bathroomsSleeps 10278.7 sq m

Popular amenities

Hot tub

Barbecue grill

Pet-friendly

Parking available

Washer

Explore the area

Chester

Tancook Island

7 min drive

St. Stephen's Church

7 min drive

Chester Art Center

8 min drive

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 King Bed and 4 Queen Beds

5 bathrooms

Bathroom 1

Bathtub

Bathroom 2

Bathroom 3

Bathroom 4

Bathroom 5

Spaces

Porch or lanai

Kitchen

Balcony

Separate dining area

Garden

About this property

NEW for 2024! The Oaks Seaside Retreat has been a historic inn, elegant personal residence and now after an architecturally inspired renovation - the most charismatic and relaxing vacation home for your family, friends, or both. With 5 private bedrooms, 5 private baths and plenty of space for everyone on that classic covered porch - there is room for the whole group.

No matter what's on your amenities list, The Oaks has you covered in fine fashion. Your own private beachfront, brick outdoor fireplace, dining area overlooking the water, carriage house complete with a dedicated gym/yoga space, pool table and even a large hot tub. We could keep going on this list, but the pics tell an even better story.

Ideal for multiple or multi-generational families, hosting small group getaways and memorably celebrating any of life's milestones together. Space for everyone where you want it, space just for you where you need it. Perfectly situated on the traditional route connecting Chester to the rest of the South Shore, everything you want to experience and explore is only a short distance away.

All of the places and spaces on your itinerary are within easy reach - SENSEA spa, the magical town of Chester, Mahone Bay and Lunenburg, pristine beaches, or how about a little Oak Island mystery? For over a century, The Oaks has been a hub to access it all.

We pride ourselves in honouring the history of this iconic home by providing a spotless property and of course, that legendary East Coast hospitality.

Property manager

Sleepyhouse

Premier Host

Languages

English

Amenities

Hot tub

Kitchen

Washer

Dryer

Pet-friendly

Air conditioning

Kitchen

Washer

Dryer

Free WiFi

House Rules

Check in after 3:00 PM

Minimum age to rent: 25

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

Events allowed

Pets

Pets allowed

Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy

Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges

Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed

Parties and events are allowed on site

Host has indicated that there is a carbon monoxide detector on the property

Host has not indicated whether there is a smoke detector on the property

Safety features at this property include a fire extinguisher and a first aid kit

Property Registration Number RYA-2022-05-17103724588676152-74

About the area

Chester Basin

Located in Chester Basin, this holiday home is on the beach. Chester Golf Club and Cocoa Organic Spa & Boutique are worth checking out if an activity is on the agenda, while those looking for area attractions can visit Have A Yarn and For The Birds Nature Shop.

Chester

What's nearby

Tancook Island - 7 min drive
Chester Playhouse - 8 min drive
Chester Golf Club - 10 min drive
Graves Island Provincial Park - 11 min drive
Oak Island - 12 min drive

Restaurants

‪Seaside Shanty Restaurant - ‬3 min walk
‪Subway - ‬7 min drive
‪Kiwi Cafe - ‬8 min drive
‪Fo'c'sle Tavern - ‬8 min drive
‪Big Red's Restaurant - ‬6 min drive

Frequently asked questions

Is The Oaks Seaside Retreat pet-friendly?

Yes, pets are allowed at this property.

What time is check-in at The Oaks Seaside Retreat?

Check-in begins at 3:00 PM.

What time is check-out at The Oaks Seaside Retreat?

Checkout is at 10:00 AM.

Where is The Oaks Seaside Retreat located?

Nestled on the beach, this Chester Basin holiday home is within 6 mi (10 km) of Tancook Island, Chester Golf Club and Bezanson Lake. Oak Island and Lordly House Museum are also within 6 miles (10 km).

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

Diane H.

15 Aug 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family Reunion on South Shore

This is a beautiful and comfortable property with a great location. It has so many different areas in the house and guest house to gather. It was a perfect place for our two families to get together. The pool table was in constant use and the kitchen was also used alot as we did all our own cooking. The host was very responsive and helpful. Would highly recommend this property to anyone looking for a great relaxing vacation.

Stayed 3 nights in Aug 2024

10/10 Excellent

Barbara S.

12 Aug 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family retreat

This was a great opportunity as a family to hang out and enjoy summer fun and learn about new places. We had the best time and our hosts were fabulous. We are excited to go back and stay at Oak Seaside Retreat again. IT WAS THE BEST!

Stayed 5 nights in Jul 2024

10/10 Excellent

Barbara S.

4 Aug 2024

Liked: Cleanliness, check-in, communication, location, listing accuracy

Family getaway

Beautiful in every way. Great location great people we will book again. Thank you Alan and Brooke

Stayed 5 nights in Jul 2024

About the host

Hosted by Sleepyhouse

We LOVE hosting families and new found friends from across the country and around the globe. Helping to provide exceptional experiences and memories that you will carry for a lifetime, that's why we love what we do.

Why they chose this property

Chester Basin is the ideal jump off spot to exploring Nova Scotia's South Shore. The endless charm of the historic villages of Chester, Mahone Bay and Lunenburg, plus less than an hour to Halifax. Top it all off with your own private cove and you will love the area as much as we do.

What makes this property unique

The Oaks is all about maintaining a long-standing local tradition - to host the most exceptional stays on the South Shore. It's all here, everything a modern traveller could want has been carefully planned and curated. Doing it great, since 1898.