Entire home

The Oaks Seaside Retreat

Photo gallery for The Oaks Seaside Retreat

Magical Mahone Bay
No agenda needed ...
A tradition of tranquility
Seaside soaking!
Surrounded in pristine landscpaing and gardens

Reviews

9.6 out of 10
Exceptional
5 bedrooms5 bathroomsSleeps 10278.7 sq m

Popular amenities

  • Hot tub
  • Dryer
  • Washer
  • Gym
  • Fireplace
  • Barbecue grill

Explore the area

Map
Chester, NS
  • Chester Playhouse
    ‪8 min drive‬
  • Chester Golf Club
    ‪10 min drive‬
  • Oak Island
    ‪12 min drive‬

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Queen Bed

Bedroom 4

1 Queen Bed

Bedroom 5

1 Queen Bed

5 bathrooms

Bathroom 1

Soap · Towels provided · Bathtub · Bidet · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 2

Soap · Towels provided · Toilet · Shower only · Shampoo · Hair dryer

Bathroom 3

Soap · Towels provided · Toilet

Bathroom 4

Soap · Towels provided · Bathtub or shower · Toilet · Shampoo · Hair dryer

Bathroom 5

Soap · Towels provided · Toilet

Spaces

Porch or lanai
Kitchen
Balcony
Separate dining area
Garden

About this property

The Oaks Seaside Retreat

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

Add dates for prices

Amenities

Hot tub
Kitchen
Washer
Dryer
Pet-friendly
Air conditioning

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House Rules

Check in after 3:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0–17
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Events

Events allowed
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Pets

Pets allowed
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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 STR2425D6908

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.
Map
Chester, NS

What's nearby

  • Tancook Island - 7 min drive - 6.9 km
  • Chester Playhouse - 8 min drive - 7.9 km
  • Chester Golf Club - 10 min drive - 9.2 km
  • Graves Island Provincial Park - 11 min drive - 11.1 km
  • Oak Island - 12 min drive - 9.7 km

Restaurants

  • ‪Seaside Shanty Restaurant - ‬3 min walk
  • ‪Kiwi Cafe - ‬8 min drive
  • ‪Subway - ‬7 min drive
  • ‪Rope Loft - ‬7 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).

Reviews

9.6

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 7 out of 9 reviews
Rating 8 - Good. 2 out of 9 reviews
Rating 6 - Okay. 0 out of 9 reviews
Rating 4 - Poor. 0 out of 9 reviews
Rating 2 - Terrible. 0 out of 9 reviews

9.6/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

10/10 Excellent

Duane L.

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

Well maintained large comfortable home.

Enjoyed our stay. Extremely comfortable beds.
Stayed 2 nights in Apr 2025

8/10 Good

Melanie M.

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

Great Stay

Overall we had a great stay, beautiful home. All you needed in the home was provided for. Carriage house was beautiful as well. Our only issue was the hot tub didn't seem clean or have enough water in it. Overall visit was great though.
Stayed 2 nights in Mar 2025

10/10 Excellent

Calinda B.

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

Fab Weekend at the Oaks

A beautiful heritage property with ample room for a girls weekend away. The bedrooms were comfortable and private. The kitchen was well-stocked and large. We would love to come back during the summer to enjoy thegardens and BBQ
Stayed 2 nights in Feb 2025

10/10 Excellent

Chrystal G.

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

Wonderful property, terrific stay

This is a gem of a property. We had 6 adults in our party and it was more than enough room. It is overlooking the beautiful bay and about 10 minutes from Chester. So many beautiful and thoughtful touches from the artwork, extra bedding, fully stocked kitchen, and the most comfortable beds with soft and lovely sheets. Alan is very responsive with all questions and check in was quick and easy. it’s nice as the actual houses, the carriage house just a few steps away above the garage is equally as quaint and impressive with amazing views. Despite it being very cold, we still sat out and enjoyed coffee just to absorb these views.. We are already planning on when we can rent this wonderful home again in warmer weather so we can truly appreciate and utilize all of it specialness. One small thing to note: while there is ample space to work out in the garage, the treadmill is quite dated, and perhaps the weights could be replenished with newer ones. That said, this is minor and does not take away from this property being one of the nicest ones at.we can’t wait to come back.!
Stayed 2 nights in Nov 2024

10/10 Excellent

Tania D.

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

Beautiful getaway

This place has so many lovely little corners that there is somewhere for everyone, even with a large group. Want to read a book on the verandah? Check. Play pool? Check. Have a full Thanksgiving sit-down dinner? Check. Do a puzzle in the sunroom? You get the idea. :) Communication was excellent and everything was well taken care of.
Stayed 2 nights in Oct 2024

8/10 Good

Garth T.

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

Tait Stay

Great property and location. Will stay again.
Stayed 2 nights in Sep 2024

10/10 Excellent

Diane H.

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.

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.

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

Host profile image
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.

Languages:

English

Premier Host

They consistently provide great experiences for their guests