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Vacation rentals in Chester

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Top-rated vacation rentals in Chester

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest suite in Hubbards

4.97 out of 5 average rating, 156 reviews

Studio Suite at Cove Cottage Eco Oasis

We're a lakefront eco-retreat* tucked into the woods, 45 mins from HRM. Walk the boardwalk or trails, sit in one of a dozen areas enjoying the views, runner ducks, or chickens. Go kayaking or swimming. Your stay includes DIY Breakfast bar: Fresh eggs, buttermilk pancakes, oats *One of 3 accommodations here. Unit Details ⬇️ Firepit wood, smores & snack boxes available seasonally. Only 30mins to Sensea Spa. Star-watching & Farmers market - a must! Find us on TT or FB: covecottageecooasis

Home in Crousetown

4.98 out of 5 average rating, 514 reviews

Cozy Riverside Cottage Indoor & Outdoor Fireplace

River music awaits you. Escape the hustle and bustle of city life to embrace tranquility of nature nestled in a tiny home on 2 acres overlooking a set of rapids. Stroll along the paths and unwind or cozy up by the fire with a good book. All this awaits you at Herons Rest. This is not just a home; it's a lifestyle! If you feel like venturing out, enjoy the beauty and fun offered by the South Shore, explore its abundant beaches, restaurants, shopping and music there is something for everyone!

Cottage in Mahone Bay

4.98 out of 5 average rating, 166 reviews

Purple Toad Cottage on Mushamush Lake, Mahone Bay

Purple Toad Cottage is a charming lakeside retreat nestled in the serene beauty of Mahone Bay. This picturesque getaway offers the perfect blend of modern comfort and vintage charm. Come for a swim, go boating and fishing in the warmer months, skating or a game of shinny in the winter. Room for 5 in the winter (2 bedrooms) or 6 with the bunkie when the weather is warm. Purple Toad is the perfect place to escape, enjoy a slower pace, gaze at the stars, exhale and revel in the sounds of nature.

Tiny home in Lunenburg

4.97 out of 5 average rating, 190 reviews

Birch tree abode-tiny hme 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 a secluded 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

Tower in Broad Cove

5 out of 5 average rating, 223 reviews

Shackup Tower - 30 ft in the air & hot tub

Perched high on an ocean hillside, built on 30 ft tall steel legs, the cozy quarters above are akin to an old ship’s cabin. With 360 views at 30ft up you can chart the sun and stars across the sky, set your rhythm to the ebb & flow of the tide and scout the surf from above. Greet the evenings with a cozy woodstove, sunset with drinks on the deck, moonrise with a dip in the hottub & mornings with fresh espresso. Permit yourself to depart land for a while and come stand watch at The Tower.

Cottage in Martins Point

4.95 out of 5 average rating, 162 reviews

OTW Close 2 Nordic Spa — Accepting Travel Nurses

• "Occupancy Fees or Property use tax" are local sales taxes charged by Airbnb (HST 15%) • 3pm Checkin • 15 mins to NORDIC Spa • 10 mins from Mahone Bay & Oak Island • Free bikes with access to the Chester Connection Trail • BBQ, full kitchen and utensils, A/C, cable TV, wifi and parking • Open-concept living • Full bath on the main floor, 2 bedrooms on the second floor • The house is 100 years old so the stairs are steep • Porch has shared laundry facilities for the guesthouse next door

Tiny home in Nova Scotia

4.97 out of 5 average rating, 200 reviews

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

Tiny home in Martins River, Mahone Bay

4.93 out of 5 average rating, 222 reviews

Pirate's Roost, a tiny house in Martins River, NS.

A bright and cosy little house just off the Lighthouse Route on a quiet dead end road that curves along the river to the mouth of the bay. The property consists of grass lawns, flower gardens, surrounding woods and a river view. Enjoy our private dock and peaceful nature walks along the water or woods during all of the beautiful seasons. Hang out in the open concept downstairs. Cook a meal inside or bbq outside. Relax in front of the fire while dozing or reading a book.

Cottage in Chester

4.95 out of 5 average rating, 110 reviews

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.

Home in Mahone Bay

4.98 out of 5 average rating, 121 reviews

Mahone Bay Ocean Retreat

Your private spa & luxury ocean getaway! Beach access, keyless self check-in. Completely private on the South Shore. Cathedral ceilings. Four seasons private spa with hot tub, full spectrum infrared sauna, indoor & outdoor rainfall showers, and indoor wet room with claw foot tub. Bbq, wireless wifi, chef’s kitchen, wine fridge, AC, wood stove, smart tv. King size bed with premium linens. A calm, luxurious space flooded with natural light and epic ocean views.

Chalet in Lunenburg

4.91 out of 5 average rating, 279 reviews

Waterfront loft with million dollar view- Suite 2

These unique and thoughtful suites, each of the three units are outfitted with subtle nuances giving the spaces their own special feel. Visitors will enjoy designer micro-kitchens, fully stocked with amenities any food enthusiast would appreciate. A cozy wood stove for those chillier evenings. All units have a special secondary sleeping nest area accessible by ladder. A serene place to hide away and watch for shooting stars through the skylight windows.

Cottage in Chester

4.98 out of 5 average rating, 114 reviews

Lovely Times Cottage - A Chester lakeside retreat

Our 4-season cottage is located just 50 minutes from downtown Halifax, 60 minutes from Halifax International Airport, 7 minutes from Chester and the Sensea Nordic Spa (open year round) and 35 minutes from Ski Martock (open Dec through end of March). With breathtaking lake views, this quiet paradise in the forest is a perfect getaway anytime of year.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Popular amenities for Chester vacation rentals

Free parking on premises

Air conditioning

Stay near Chester's top sights

SENSEA Nordic Spa39 locals recommend

The Kiwi Cafe44 locals recommend

The Rope Loft36 locals recommend

Fo'c'sle Tavern29 locals recommend

The Stretch Diner5 locals recommend

Oceanview Home and Garden3 locals recommend

Other great vacation rentals in Chester

Cottage in Chester

5 out of 5 average rating, 18 reviews

Spectacular 5 Bedroom Spaview Retreat!

Home in Chester

5 out of 5 average rating, 7 reviews

Hidden Hideaway: Close to the Nordic Spa

Tiny home in Maitland

4.96 out of 5 average rating, 68 reviews

Lakefront Tiny Home ~ Hot tub

Bungalow in Chester Basin

5 out of 5 average rating, 95 reviews

Ocean Front Home Chester Basin

Cottage in Lunenburg

5 out of 5 average rating, 32 reviews

A Secluded Lakefront Spectacle

Cabin in Mahone Bay

4.9 out of 5 average rating, 52 reviews

The Narrows Nest

Rental unit in Lunenburg

4.98 out of 5 average rating, 41 reviews

"lil" HOOKs - "lil" GEM.

Home in Chester

4.98 out of 5 average rating, 47 reviews

The Whale House

Quick stats about vacation rentals in Chester

Total rentals
50 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
900 reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Chester?
Yes! Work meets play with ease at over 20 vacation rentals in Chester featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Chester?
Four-legged friends are welcome in Chester. Choose from more than 20 vacation rentals for guests traveling with pets.
Do house rentals in Chester have self check-in?
Absolutely! We offer over 10 house rentals with self check-in in Chester. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Chester?
Experience the best of Chester with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly house rentals in Chester?
Chester has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Chester have wireless internet?
Absolutely! We offer over 30 house rentals with wireless internet in Chester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chester have a bbq area?
Absolutely! We offer over 10 house rentals with a bbq area in Chester. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Chester?
Enhance your stay in our House Rentals with the most popular amenities: over 10 homes with self check-in, over 10 homes with a bbq area, over 30 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

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