Intrigued by the mystery surrounding the Oak Island treasure? Why not visit and explore Oak Island’s history - maybe you’ll be the one to find it! All jokes aside, Oak Island is rich with history and culture. Whether you’re a fan of history or not, you will definitely enjoy this one. Tours are also available all-year-round, regardless of the weather unless it’s too dangerous. It is teeming with museums overflowing with culture and artefacts. You can even visit the Money Pit which fuels the mystery that surrounds the alleged treasure. Otherwise, you can visit Mahone Bay and Back Harbour or even go island hopping for some breathtaking views. At the end of the day, you will need comfortable accommodation to suit all your needs. Here are the 10 best Vrbo vacation rentals near Oak Island, Chester! Read on to find the perfect one for you!
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on October 23, 2024.
Why Trust Trip101?
✅ Over 50,000 articles reviewed and published by our experienced team
✅ Over 50 years of combined experience researching, writing and reviewing travel articles
✅ Over 40,000 hours spent on research and fact-checking from credible sources (last year’s data)
✅ Optimizing content from data-driven insights collected directly from users on our platform
✅ Focus on authentic and up-to-date information by collaborating with local guides, global travelers and other industry experts
✅ Long-standing partnerships with credible brands like Airbnb, Booking.com, Agoda, Expedia, GetYourGuide, Viator, RVShare and more
✅ Full disclosure on any partnerships or sponsored content
Trip101’s team of writers, editors, and content managers oversees the publication of all travel content, including destination guides, accommodation recommendations, and travel tips. They have extensive experience in the travel industry and no content, written or visual, gets published without a review. Many of our team’s work has also been featured in Travel+Leisure, National Today, The Indian Express, The Telegraph (India), Robb Report, The Adventure Handbook, Tripoto, Korea Tourism Organization, and Korean Ministry of Culture, Sports and Tourism. Some of them are also members of professional organizations like the Society of American Travel Writers and the International Travel Writers and Photographers Alliance.
Each member of the team follows Trip101's methodology and strict editorial guidelines to ensure accuracy, authenticity, and relevance.
1. A home with an authentic Nova Scotia architecture (from USD 247)
Fall asleep to the rhythmic waves as you admire the sunset and wake up with a beautiful view of the deep blue Atlantic ocean. You’ll get to enjoy the tantalising ocean breeze in this beautifully built home. It features an authentic Nova Scotia architecture and is fully furnished. The kitchen even comes with supplies you will need to try cooking your very own Nova Scotian meals! However, if you wish to dine out, you have a variety of choices nearby too: Big Red’s Pizza, Moe’s Grill and Dining Lounge, and Island View Restaurant! Additionally, you can even see the World Famous Oak Island right on the patio. Being between Chester and Mahone Bay you will surely be greeted by breath-taking sceneries during your drive here!
Top guest reviews
Host:
though we never met them they were very responsive to our questionsLocation:
most of all it was peaceful - located on a quiet side roadRead more reviewsAmenities & Room:
beds were super comfy as was the living room furniturecomfy beds good host and charming old place with a lovely view of the water
2. A charming cottage right by the ocean (from USD 141)
This beautiful home is right by the seaside in a sheltered cove where you and your loved ones can even go swimming or kayaking! The master bedroom also provides a perfect view of the ocean so you can fall asleep to the sunsetting and wake up to the sun rising due to its two glass walls. You might even get to catch a glimpse of wildlife like eagles, deers and ospreys! Moreover, its deck comes with picnic tables and barbecue grills and its porch is screened. Perfect for relaxing! You can also be assured that the home is in pristine conditions and is extremely comfortable! The owner will even share their restaurant recommendations as well as fun things to do around the vicinity!
Top guest reviews
Host:
xedxb8x80 the owners gave us perfect directions to cottagejane our host was wonderful and kindvery caring hosts we will be backhosts where very helpful and while attentive to our needs were not intrusivethe owner is very kind and maintains the property beautifullyLocation:
great location for close proximity touring in all directionsit was nice and central to everything we wanted to seewhat a lovely place to kick back and enjoy the peace and beautyit was in a great location for day trips to chester halifax mahone bay and lunenburglots of good places to eat and boutique shopping in the nearby towns of chester & mahone bayCleanliness:
the cottage was cozy and clean with everything requred to make the stay carefreeRead more reviewsAmenities & Room:
beds were cozy furniture included some amazing antiquesthe cottage is very comfortable & cozywe loved sitting out front of the cottage for breakfast while taking in ocean views
3. A nature lover's paradise (from USD 243)
This spacious home is in the middle of a flower garden, lush lawn and a charming apple orchard. A beautiful view will greet you anywhere you look. Moreover, you will have private access to the waterfront inclusive of a floating dock and wharf. You can be sure of your safety as it also comes with anchorage! The home is fully furnished and comes with rich cherrywood flooring. The kitchen is spacious so you and your loved ones can comfortably cook up a feast in it! The dining area is equally spacious and if you fancy an outdoor meal - rain or shine - the dining room leads right to a covered deck verandah. It even comes with a fireplace to keep guests cosy and warm during winter!
Top guest reviews
Host:
paul is very attentive and professional a true gentleman who took care of ushes always responsive and professional to deal withhe's always responsive and professional to deal withLocation:
lovely property in a great locationthe facility location privacy was perfect myself and familyideal location for south shore excursionsmany thanks for supply a great place to vacationRead more reviewsCleanliness:
the place was very clean good location
Premier Host
4. A one-of-a-kind chalet (from USD 106)
Despite its unique interior, this cottage is both spacious and cosy! It is fully furnished and holds an open-plan living room with cable television and DVD as well as art and craft materials, puzzles and games to keep you and your little ones entertained during your stay! The kitchen is also fully equipped so you can cook up a storm and share a delightful meal with your loved ones. If you fancy outdoor cooking, there is also a barbecue grill for you to use. There is also a loft area which the little ones will definitely love. It provides a spectacular view for the oceanfront and has a cosy seating area. The best part? The front yard is spacious and leads right to the rocky shores!
5. A beautiful home with a modern touch (from USD 112)
A hideaway perfect for any couple! Whether you wish to simply relax together, away from life’s stresses or pamper yourselves, you will love everything the home has to offer. It’s extremely spacious with beautifully decorated interior and exterior. The kitchen is fully equipped for home-made dinner dates or if you wish to spice things up, it comes with a barbecue grill for outdoor cooking! You can even relax and rejuvenate in the spa-like ensuite anytime you please! Nonetheless, if you both wish to indulge in some shopping or exploring, Mahone Bay is nearby. You can indulge in delicious cuisines, shop ‘til you drop or even hike and cycle! Perfect for a short and fun-filled getaway.
Top guest reviews
Read more reviewsLocation:
so many neat towns close by to visit as wellbeautiful spot nice and close to town but still felt very privatevery easy to locate and close to town and the grocery store
6. A bright and spacious cottage (from USD 114)
Another cottage perfect for couples. If you are a fan of a minimalistic interior that is bright and spacious - this is it! A luxurious and charming cottage that features a gourmet equipped kitchen for you to bring out your inner master chef and an ensuite where you can enjoy a spa and soothe your tired muscles! It is also inclusive of a barbcue grill if you fancy some outdoor cooking. It even comes with free Netflix for you and your loved one to catch up on your favourite movies and shows! Shops, galleries and hiking trails are a few minutes away too. Relax and escape from life’s trouble even for a little bit!
Top guest reviews
Host:
owners pam and david are delightful and very helpfulRead more reviewsLocation:
this is the perfect location quiet but close to everythingthis cottage is perfect sparkling clean beautifully decorated great location right in mahone bay
7. A private home in a perfect location (from USD 126)
Cape Cod home is extremely near multiple towns. Whether you wish to go swimming, shopping, enjoy delectable cuisine or even go to a yacht club, you can do so with ease. Despite its seemingly small size, don’t be fooled as it comes with a spacious main floor with an open concept, an outdoor deck where you can barbecue or merely dine outdoors and a large family room! Hence, you can comfortably relax together with your family and loved ones here. There’s definitely sufficient space for eight people. The master bedroom comes with a king-sized bed and a private bathroom inclusive of a claw-foot tub. Moreover, it’s just a short walk away from the harbour, making it extremely convenient to get here. You can even park up to two cars!
Top guest reviews
Host:
the owners are amazing very kind and were available to answer our questionsphilip was a very responsive hostLocation:
great location and very well kept housethis is a beautiful house just a short walk from the centre of chesterit is well stocked and a perfect location for touring in either direction: toward lunenburg or halifaxRead more reviewsAmenities & Room:
we were there at christmas and were delighted with the decorated tree in the living room
8. A beautifully decorated home for three (from USD 111)
A quaint and well-kept home perfect for small families or couples; a truly beautiful home with carefully designed interiors. From colour palettes to door frames, everything was chosen with great consideration. The bathroom features a stand-up shower and comes with complimentary bath products. The backyard is fenced and has foliage so you can be sure that you will have your privacy. It is directly connected to the provincial hiking and cycling trails. Moreover, two mountain bikes are provided just for you! For sports enthusiasts, sailing, kayaking tours and golfing are available nearby too! There are also carriage rides, on-site wine tastings and white sand beaches available within the vicinity.
Top guest reviews
Host:
jay was very helpful quick to answer questions or help with concernsjay was very knowledgeable of the area and very responsive to questions we hadowner was friendly and helpful - with discounts and recommendations on nearby hauntshe was easy to communicate with very laid back and overall the perfect hostyou couldn't ask for a more convivial and conscientious hostLocation:
terrific place cute and well appointedwe enjoyed the quiet ambiance the trail for private walks and the close-to-everything locationhe arranged a room for us at the marina close by which was greatthis is a very comfortable cottage close to south shore attractionsthe cottage is within close driving distance to a lot of attractionsCleanliness:
the guesthouse was clean well maintained and very nicely decoratedthe aesthetic is clean uncluttered and welcomingthe house is very cleanthe property was cleanowner was very helpful and the cottage was clean and well kept (bathroom a tad small)Read more reviewsAmenities & Room:
air conditioning in the bedroom made for a great sleepwe prepared most meals in the cottage taking advantage of the fully equipped kitchenkitchen bath office bedroom livvingroom - all theese rooms are good to live inwe noticed some additional details like tea or a bottle of wine in the basket on the table
9. A unique and carefully decorated home (from USD 203)
A spectacular view of the ocean from every window is what you can expect here. This beach house is on a cove, allowing guests to simply step outside for their very own small, private beach. You can even see the famous Oak Island from here! On top of that, it has a back deck with an outdoor shower for you to use after dipping in the ocean as well as a barbecue for you to share a delightful meal with your loved ones. Each bedroom comes with a comfortable queen-sized bed and reading lights for you to relax in after a long day at the beach. Not only is the exterior and surroundings beautiful but the interior is too; it was self-restored by the owner. Hence, every inch of the house was specially designed and is extremely unique!
Top guest reviews
Host:
our host jay could not have been more helpful and accommodatingRead more reviewsLocation:
very pretty and quiet location but only a short drive to chester and mahone bayawesome serene location on the water with super comfortable casually modern stocked space
10. A beautiful oasis surrounded by nature (from USD 454)
This home features spacious bedrooms with extremely comfortable bedding for you to snuggle up on after a long day of fun in the sun. It even has a sunroom that has a spectacular view of the beautiful back garden teeming with exquisite flowers and mature trees. There’s even a flagstone patio with a trickling water feature. Furthermore, it’s fully fenced so you can be certain of your privacy. Nonetheless, this beautiful home is minutes away from Chesters Front and Back Harbours - home to numerous shops and restaurants. If you wish to soak up the sun or go swimming, it’s near Freda’s Beach too! With the multitudinous activity centres and attractions nearby, you are spoiled for choice. A fun-filled adventure awaits you here!
Top guest reviews
Host:
pauline is an excellent hostthe owners thought of everything to make it the perfect family vacation homeour host pauline was very easy to deal with and always reachablepauline was wonderful and responsive and a pleasure to work withthe owners were easy to work with -- very easy and quick communicationLocation:
a perfect location for our family and friends to spend a few summer weeksit is in a lovely location in chesterthe house is in amazing shape and is an easy walk from pubs restaurants and the beautiful harbourCleanliness:
clean modern and well equipped with thoughtful and responsive ownersthe house itself is beautiful spacious and cleanthe house was well equipped spacious comfortable spotless and perfectly designed for entertaining groups of peopleRead more reviewsAmenities & Room:
the rooms and furnishings were inviting and comfortablethe house is large nicely decorated with comfortable furnitureour two families were very comfortable during our week at the lovely chester garden house
Pamper yourselves, book a home today
A weekend getaway or a week-long getaway, one of these homes is sure to tickle your fancy. Don’t hold back and book one today! Your mental well-being is essential too. Remember to take some time off and pamper yourself and your loved ones.
History
Get Trip101 in your inbox
Unsubscribe in one click. See our Privacy Policy for more information on how we use your data
