Holiday rentals in Chester

4.98 out of 5 average rating, 314 reviews

Tiny home in Lunenburg

Birch tree abode-Bunkie with dry/wet CEDAR SAUNA

Welcome to ‘Birch Tree Abode’. A unique way to unwind after a day in lunenburg county.Situated between Lunenburg and Mahone bay. Minutes from either. This bunkie’ is situated amongst the trees, with comfortable deck to enjoy the beginning/end of your adventures around the South Shore. A beautiful open plan living space, high end bathroom, all rustically finished . 400sq ft-this is slightly larger than a ‘tiny home’, however minimal space 4 storage/luggage ,also note 5.10 ceiling in bedroom area

4.94 out of 5 average rating, 114 reviews

Villa in Chester

Chester Oceanfront Luxury Villa

Welcome to Skipper Hill, where you will find this stunning villa nestled in the corner of the community, on a 178' oceanfront lot! Enjoy being 10 minutes from both SENSEA Nordic Spa, and Chester Village - where you'll find a selection of restaurants, cafes, and shops sure to please any discerning traveller. Our villa was professionally built and decorated in 2020, thoughtfully prepared for both short and long stays. You'll love the uninterrupted ocean views, countless windows capturing the ocean

5 out of 5 average rating, 64 reviews

Charming Chester cottage steps from Nordic spa

Monthly + weekly discount available No HST (tax) on stays over 30 days A restored century-old east coast cottage steps away from the Rum Runners nature trail. A quick walk to a serene lakeside Nordic spa, as well as Chester village pubs, restaurants, shops, yacht club + saltwater pool overlooking the ocean on Nova Scotia’s coveted South Shore. Peggy’s Cove, Mahone Bay+ Lunenburg are nearby, as are poular golf courses + glorious beaches. Halifax is 50 minutes away. Registration: STR2526D8211

Superhost

Cabin in Martins Point

4.92 out of 5 average rating, 191 reviews

FFA Close to Nordic Spa — Accepting Travel Nurses

• "Occupancy Fees or Property use taxes" is the mandatory local sales tax charged by Airbnb (HST 15%) • 3pm Checkin • 15 mins from NORDIC Spa • 10 mins from Mahone Bay • 3 mins from Oak Island • Free bikes provided with access to the Chester Connection Trail • A/C, cable TV, wifi & free parking on site • Cozy & comfortable with a large back deck, BBQ. Stand up shower only. • Please note it is a cottage with 7' ceilings (not 8') • The second bedroom is best suited for a child (more info below)

4.98 out of 5 average rating, 162 reviews

Tiny home in Maitland

Lakefront Tiny Home ~ Hot tub

Lakefront access and water views with stunning sunsets greet you from the hot tub! Spacious and bright, this tiny home features: -Queen bed loft 🛏️ -Pull-out sectional with queen-sized sleeping area 🛋️ -Stocked kitchen with full-size appliances 🧑‍🍳 -3 piece bathroom with shower 🚿 -Deck for enjoying water views and sunshine ☀️ -Beautiful quiet lake 🌊 Only 10 minutes to the tourist hub of Mahone Bay, and 15 minutes to Lunenburg! Discounts when booked with the cottage on the property.

4.96 out of 5 average rating, 224 reviews

Tiny home in Nova Scotia

Cozy Cottage on South Shore. 30 min from Halifax!

A very cozy and peaceful place to base any vacation on the South Shore out of. Very close to hiking and ATV trails. No visible neighbors from the yard, lots of wildlife. Large parking areas. Interior is a mixture of new and re purposed materials. Appliances are small but functional, all the comforts of home but smaller. Double bed is incredibly comfortable. It is my home that I vacate for guests, and contains some sentimental decorations and items. RYA-2023-24-03271525339628999-1197

4.97 out of 5 average rating, 818 reviews

Cabin in LaHave

East Coast charm, cabin and hot tub by the river

The perfect location to explore the very popular South Shore of Nova Scotia. Close to beaches, cafes, restaurants, charming fishing villages and many other amenities. Come for a magical getaway. Tucked away in the woods along side a babbling brook. Enjoy morning coffee on the deck, BBQ your dinner overlooking the river, groove to our vintage record collection, keep toasty by the wood stove and float in the hot tub under the stars. This is a wonderful cabin experience you won't forget!

4.96 out of 5 average rating, 338 reviews

Guest suite in Lunenburg

A Suite Stay!

Whether you are looking for a weekend get away or have business in the local area, we have the perfect place for you. Just 3 minutes from Mahone Bay, 7 from Lunenburg and 25 minutes from Sensea Nordic Spa in Chester. Enjoy the convenience of a full kitchen, relaxing living room, spacious bedroom and bathroom! Enjoy an outdoor fire pit after a day of exploring! Please note : Our grandchildren are now living with us and therefore we are unable to guarantee complete silence.

4.96 out of 5 average rating, 125 reviews

Cottage in Chester

Moss Cottage on the Lake

Moss Cottage can be your getaway only 45 minutes from Halifax and a few kilometers from the village of Chester on Nova Scotia's beautiful south shore. It's your choice to take in the many local sights, shop in towns and villages that dot the coastline, sail, play golf or stretch out on any number of beaches -- all within easy driving. Or, perhaps you'd prefer to stay put at Moss Cottage for a lovely chance at solitude and a dip in our crystal clear, spring fed lake.

4.98 out of 5 average rating, 177 reviews

Home in Mahone Bay

Mahone Bay Ocean Retreat

Your luxury ocean getaway and private spa for two. Private beach access, keyless self check-in. On the beautiful South Shore minutes from town. Cathedral ceilings & epic views. Four seasons. Hot-tub, full spectrum infrared sauna, both indoor & outdoor rainfall showers. Indoor wet room with claw foot tub. Bbq, wireless wifi, chef’s kitchen, wine fridge, AC, wood stove, Netflix, and King size bed with premium linens. A calm, luxurious space flooded with natural light.

4.95 out of 5 average rating, 220 reviews

Guest suite in Hubbards

Studio Suite at Cove Cottage Eco Oasis

We're a lakefront eco-retreat tucked into the woods, 45 mins from HRM. Walk the boardwalk, sit lakeside enjoying the views or enjoy the ducks & chickens. Star-watching is a must! Your stay includes a DIY Breakfast bar: Buttermilk pancakes, chocolate chips, syrup, rolled oats & oatmeal pkgs Studio Suite is an Apartment here in our main building, more detail ⬇ Find us on TT, IG & FB: covecottageecooasis

4.99 out of 5 average rating, 105 reviews

Home in Lunenburg

Ocean Front #12 HotTub PrivateDeck waterfront BBQ

Take it easy at this unique and tranquil getaway.and a waterfront deck brimming with amenities. Enjoy the comforts of home and beyond with air-conditioning, a fire pit, and more in this private community oasis. Complete with a private pier and boat launch, HOOK'd 12 invites you to experience waterfront living at its finest, just moments away from the heart of Lunenburg village.

Holiday rentals for every style

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Kick off your hiking boots at these rustic lodgings

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Quaint homes, peaceful surroundings

Popular amenities for Chester holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Chester

4.97 out of 5 average rating, 97 reviews

Home in Seabright

Dome in the Woods

PedroRating, 5 starstoday

The place was very organized and welcoming. It had everything we could need, it was in a very clean condition, and very well equipped. There was a guide with things to do and places for food. One thing to keep in mind is that there is an open roof so id recommend bringing eye masks. It was fun watching the wild life out the window.

4.98 out of 5 average rating, 48 reviews

Cabin in Lunenburg

Lakefront Luxury Retreat

RuslanaRating, 5 stars3 weeks ago

We had a truly wonderful stay! Everything was exactly as described — peaceful, clean, and thoughtfully prepared. We especially appreciated the attention to detail — it’s clear that the hosts care deeply about their guests’ experience. The nature around the place is absolutely beautiful, and the quietness made it feel like a real retreat. Thank you for such a lovely atmosphere. We’d be happy to return someday!

Superhost

4.9 out of 5 average rating, 10 reviews

Endeavour Cottage

ShelbyRating, 5 stars2 weeks ago

This was a fantastic place to stay as it was clean, thoughtfully equipped, and architecturally beautiful. My girlfriends and I booked the cottage for a cozy night in after a visit to the nearby Nordic spa, and it exceeded our expectations. The space was inviting with plenty of amenities that made our stay comfortable and relaxing. The only drawbacks were related to lighting. There were no lamps in the whole cottage, so we had to rely on the overhead lights, which made the atmosphere feel less cozy in the evening. Additionally, while the majority of the windows are not designed for curtains, it would have been nice to have some window coverings in the one bedroom downstairs where they could be hung to help block out the morning light. Overall, it was a wonderful experience, and we’d absolutely stay again.

4.97 out of 5 average rating, 32 reviews

C’scape Cozy getaway Chester, Nova Scotia, Canada

SherriRating, 5 stars7 months ago

Perfect for couples or solo travelers. Walkable town and shopping. Spotless accommodations and beautiful decor. Looking forward to returning again!!

4.97 out of 5 average rating, 33 reviews

Home in the Heart of Chester

RachelRating, 5 stars1 month ago

Beautiful home in the perfect location! We had everything we needed and were most comfortable! Bright and so well decorated! Our son was playing in a golf tournament which was very close by allowing us to come back and forth while we waited. Always enjoy visiting the pretty town of Chester!

4.98 out of 5 average rating, 55 reviews

The Whale House

LeeAnneRating, 5 stars1 week ago

Our stay at The Whale House was perfect! Located in the heart of Nova Scotia’s South Shore, this stunning home is a true treasure! It offers breathtaking views of a peaceful dock filled with boats and sailboats. Gretha was a fantastic host—her directions were clear, & her warm, flexible approach to check-in made us feel immediately at ease. Gretha was incredibly responsive & helpful throughout our stay, always just a message away. The home is immaculate & tastefully decorated with charming whale-themed accents. The cozy pillows & unique artwork add character & coastal charm. We loved the spacious kitchen, especially the oversized island where we enjoyed family meals and games. The large entryway, comfy beds, and thoughtful details made it feel like home. The location was ideal—close to beaches, waterside restaurants, shopping, & the famous Shore Club lobster supper. We woke each morning to the sound of song birds! We’re so grateful to Gretha for sharing her beautiful home with us.

Tiny home in Chester Grant

4.92 out of 5 average rating, 79 reviews

Lakefront tinyhome Chester Grant with hot tub

DanielleRating, 5 stars1 week ago

What a perfect getaway for my daughter and I for her prom weekend nights. So peaceful and serene I couldn’t have asked for a better location. The only thing I would say is the Wi-Fi wasn’t super great for us, but we have very old phones and we weren’t very much concerned about it either because we were away to get away not to be on Wi-Fi. Maybe it was working better if we had to try it more than a couple of times but we just threw our phones away and enjoyed what we had there. I highly recommend this place and I would definitely go back.