
Holiday houses in Chester
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Top-rated holiday rentals in Chester
Guests agree: these stays are highly rated for location, cleanliness and more.

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

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

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!

Cozy Lakefront Cottage w/ wood stove near Martock
This pet friendly, four season cottage is the perfect space to escape the city with a loved one for a weekend or for your next family vacation! Only 50 minutes from Halifax, it’s in perfect proximity between downtown Chester and Windsor. The home Includes a large eat in kitchen with sitting area, bathroom, laundry and two bedrooms on the main level and a walkout primary bedroom and large living room with wood stove on the lower level and a large walk out deck overlooking the lake.

The Boathouse on Scotch Cove
This little boathouse sits right on Scotch Cove in East Chester, NS. Enjoy seaside views from every angle, with lovely outdoor seating and propane BBQ. The deck leads directly to the dock allowing for easy access for swimming or watercraft provided. The place is just a short walk from hiking and biking trails, with nearby lakes and sandy beaches. The indoor projector and screen make movie nights so much better! The boathouse is fully equipped for winter with a cozy woodstove.

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.

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.

Pleasant Street Suite
Location, location, location! This studio apartment is located in the heart of Mahone Bay. Restaurants, shops, grocery store, pharmacy, and of course the three churches are within a 5 minute walk. The space is colourful and cheery with an east coast vibe. The apartment has a well equipped kitchenette if you prefer to cook light meals yourself. There is also a dining area which could be used as a very comfortable work space. Enjoy our beautiful town!

Ocean Front #3 HotTub Sunset RoofTopDeck BBQ 2bath
Waterfront Cottage: Huge deck, sun sets, Private Hot Tub: 6 Person tub for 2. Panoramic Water Views: Modern Cabin: privacy and a peaceful environment. Large Deck: outdoor living space both you can take in the sun or retreat into the share. Nature Retreat with wildlife Romantic Escape: for couples, Heated floors, Shower tower, queen master, an extra guest could sleep on the couch. Super private chefs kitchen. Well equipped for all seasons.

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! Meet our greeters, Max & Ruby. They love to see everyone!!

Peaceful 2-Bedroom Coastal Cottage 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.

Hutt Lake Studio 10 minutes away from Sensea Spa
Relax and unwind at this unique and tranquil getaway. Air conditioned for your comfort. Steps away from a lake for you with private beach to enjoy. Kayaks and pedalboat for you free to use at your own risk. Central location with Mahone Bay, Lunenburg, Peggy’s Cove and Halifax all a very easy drive from your cottage. Very quiet and peaceful location.
Popular amenities for Chester holiday rentals
Stay near Chester's top sights
Other great holiday rentals in Chester

Steel the Wave

White Cottage

One 12 Queen - EV Charger

Chester Suite By The Ocean

The Twee House at Meisners Beach

Marigold Cottage Luxury Suite

Lavender Suite - The Dordean Suites of Chester

Oceanfront #6 Hot tub sun sets huge deck BBQ 2 bed
When is the best time to visit Chester?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $231 NZD | $233 NZD | $218 NZD | $240 NZD | $248 NZD | $305 NZD | $347 NZD | $412 NZD | $313 NZD | $300 NZD | $240 NZD | $303 NZD |
| Avg. temp | -6°C | -6°C | -2°C | 4°C | 10°C | 14°C | 17°C | 17°C | 14°C | 9°C | 4°C | -2°C |
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 a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Chester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chester have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning 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 $50 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 30 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Chester have free parking?
Absolutely! We offer over 30 house rentals with free parking in Chester. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Chester have wifi?
Absolutely! We offer over 30 house rentals with wifi in Chester. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Chester

Total holiday rentals
Explore 50 holiday rentals in Chester

Nightly prices starting at
Chester holiday rentals start at $84 NZD per night before taxes and fees

Verified guest reviews
Over 1,590 verified reviews to help you choose

Family-friendly holiday rentals
40 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
50 of Chester holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Chester rentals

4.9 Average rating
Chester stays are highly rated by guests—averaging 4.9 out of 5!
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- Oak Island
- Rissers Beach Provincial Park
- Hirtle's Beach
- Halifax Citadel National Historic Site
- Rainbow Haven Beach
- Conrad's Beach
- Canadian Museum of Immigration at Pier 21
- Lawrencetown Beach Provincial Park
- Point Pleasant Park
- Ski Martock
- Halifax Public Gardens
- Maritime Museum of the Atlantic
- Halifax Central Library
- Kejimkujik National Park & National Historic Site
- Crystal Crescent Bch Provincial Pk
- Shubie Park
- Fisherman's Cove
- Dalhousie University
- Peggys Cove Lighthouse
- Luckett Vineyards
- Grand-Pré National Historic Site
- Halifax Waterfront Boardwalk
- Big Mushamush Lake
- Museum of Natural History




