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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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Farm stay in Blockhouse

4.8 out of 5 average rating, 459 reviews

Cottage Farm Oasis Mahone Bay- Hottub Goats Nature

May 3wk SPECIAL Rate! Retreat to beautiful heritage farm sanctuary nr Mahone Bay & Bridgewater. Popular with Sensea Spa. Charming studio cottage: privacy & nature <1hr to Halifax. Perfect romantic getaway or solo/friend escape - unwind & recharge. BBQ, firepit, Wifi/smartTV, boardgames, heat pump/AC. Hike, goat cuddles. Optional Hottub, pizza oven etc.. *No pets. Options: hottub, wood-fired pizza oven, brekkie, charcuterie, cheesemaking class. See below for add-ons $s. * May block bkg discount!

Mar 19 – 26

Tiny home in Lunenburg

4.97 out of 5 average rating, 140 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

Oct 5 – 12

Home in Crousetown

4.98 out of 5 average rating, 501 reviews

Cozy Riverside Cottage Indoor & Outdoor Fireplace

River music awaits. Escape the hustle and bustle of city life to embrace tranquility of nature nestled in a tiny home on 2 acres along a picturesque river. 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!

Jan 30 – Feb 6

Dome in Chester

4.95 out of 5 average rating, 136 reviews

Norse Geodesic Retreat (Balder)

Embrace the cozy allure of fall in our geodesic domes, cocooned by nature's vibrant transformation. Sip complimentary hot chocolate and wine on your private deck, soak in your private hot tub. Bask in climate-controlled comfort and take in the breathtaking fall foliage. Enjoy thrilling moments at Ski Martock or explore the lake with our kayaks from our access point. Just 45 minutes from Halifax, our domes offer an autumnal escape for couples seeking reconnection amid the season's splendor

Mar 27 – Apr 3

Cottage in Martins Point

4.95 out of 5 average rating, 147 reviews

Over The Way Cottage — close to Nordic Spa

• "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

Nov 30 – Dec 7

Tower in Broad Cove

4.99 out of 5 average rating, 196 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.

Jan 7 – 14

Tiny home in Nova Scotia

4.96 out of 5 average rating, 190 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

Jan 30 – Feb 6

Home in Mahone Bay

4.97 out of 5 average rating, 103 reviews

Mahone Bay Ocean Retreat

Your private 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. King size bed with premium linens. Licensed esthetician bookings available. A calm, luxurious space flooded with natural light and epic ocean views.

Aug 7 – 14

Guest suite in Hubbards

4.97 out of 5 average rating, 120 reviews

Lakefront Eco Oasis, Cove Cottage Studio Suite

A lakefront eco-paradise tucked into the woods, only 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 a DIY buttermilk pancake & oat breakfast bar. Farm fresh eggs, fruit, veg, firepit wood & smores available seasonally. Only 30 from Sensea Spa. Star-watching & Farmers market - a must! Find us on TT or FB: covecottageecooasis No dogs - allergies!

Dec 3 – 10

Cottage in Chester

4.95 out of 5 average rating, 104 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.

Sep 23 – 30

Cottage in Chester

5.0 out of 5 average rating, 28 reviews

Cozy Oceanfront Escape with Hot Tub

High above the ocean, this contemporary two-bedroom cottage provides sweeping coastal views, stunning sunsets, and a canopy of starry skies. Overlooking the entrance to Deep Cove, and out towards Chester, Nova Scotia, this secluded four-season cottage offers an idyllic escape, ideal for a romantic couple's getaway or a tranquil retreat from the everyday.

Dec 2 – 9

Guesthouse in Chester

5.0 out of 5 average rating, 20 reviews

The Little Caboose

Enjoy easy access to everything from this centrally located place in Chester. Short walk to SENSEA Nordic Spa, several restaurants and shops, theatre, minutes from The Chester Golf Course, the Chester Trail backs on property for great hiking, biking, 4-wheeling or just a leisure stroll. Enjoy the Farmers Market on Fridays (seasonal) and so much more!

Dec 29 – Jan 5

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 Rope Loft36 locals recommend

The Kiwi Cafe44 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

Apartment in Marriotts Cove

4.88 out of 5 average rating, 42 reviews

Sailors’ Paradise - Stevens Cove Guest Quarters

Feb 14 – 21

Home in Chester

5.0 out of 5 average rating, 42 reviews

Charming three bedroom century home In Chester

Dec 11 – 18

Apartment in Chester

4.78 out of 5 average rating, 9 reviews

Marigold Cottage Luxury Suite

Nov 9 – 16

Cabin in Mahone Bay

4.91 out of 5 average rating, 46 reviews

The Narrows Nest

Dec 13 – 20

Guesthouse in Chester Basin

4.85 out of 5 average rating, 65 reviews

Hutt Lake Studio 10 minutes away from Sensea Spa

Nov 9 – 16

Home in Western Shore

5.0 out of 5 average rating, 46 reviews

Little Pink Cottage

Oct 28 – Nov 4

Cottage in Chester

5.0 out of 5 average rating, 14 reviews

Spectacular 5 Bedroom Spaview Retreat!

Feb 4 – 11

Villa in Chester

4.93 out of 5 average rating, 67 reviews

Chester Oceanfront Luxury Villa with Outstanding D

Sep 19 – 26

Quick stats about vacation rentals in Chester

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

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 10 vacation rentals for guests traveling with pets.
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 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.
Do house rentals in Chester have wifi?
Absolutely! We offer over 20 house rentals with wifi in Chester. Enjoy a tailored experience with all the comforts you desire.

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