Home Vacation Rentals By Owner In Chester, NS

Showing 32 Of 32 Vacation Rentals
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Exceptional(25)

$296.54

/ Nightly
Condo

The Captain’s Quarters 2 bedroom harbourview condo

Chester, Nova Scotia, Canada

Located in the heart of sea-side Chester, Nova Scotia with a gorgeous, full view of the front harbour. The Captain’s Quarters is a bright and beautifully finished, spacious, 2-bedroom condo that is central to all that scenic Chester has to offer. Walking distance to the pubs, restaurants, bakery, yacht club & much more! Large, floor-to-ceiling windows offer a perfect view of Mahone Bay. br brConnect easily to the whole-home surround sound system via Bluetooth, FM radio & more. 9-foot ceilings, air conditioning, brand new high-end furniture. Comfy leather swivel chairs to settle into with your morning cup of coffee and a 8 foot granite kitchen island that seats 6. The living room area features a convenient, remote-controlled electric fireplace below a wall-mounted television set up with streaming services. Both bedrooms are immaculate, with one adjacent and connected to the bathroom. brbrLess than a 5-minute drive to Sensea Nordic Spa - a perfect home base for your South Shore stay.
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Sleep 5

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$301.23

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Private Vacation Home

The Nest at Deep Cove

Chester, Nova Scotia, Canada

The Nest at Deep Cove is perfectly perched above one of the quietest little nooks on the world famous Mahone Bay. The boating, the fishing, the beaches, the cuisine, the trails, the endless East coast charm everywhere you look - you won't know which one is your favourite!brbrOur cottage boasts an EV car charger, patio overlooking the ocean, 2 beds/2 baths, BBQ area, full service kitchen, spacious ocean view living areas and comes fully complete with everything you will need to make your vacation an absolute smash hit with everyone.brbrIf a peaceful retreat is the name of the game, the Nest at Deep Cove is exactly what you have been looking for. Scenic drives into Chester, Mahone Bay, Oak Island (Western Shore), Lunenburg & only 45 mins from Halifax. brbrRead the reviews, fall in love & let's ensure your vacation surpasses expectations.brbrbrbrNova Scotia Tourist Accommodation - STR2627D4550
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Bath 2

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Sleep 6

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Exceptional(29)

$598.66

/ Nightly
Private Vacation Home

Family Home In the Heart of the Village of Chester

Chester, Nova Scotia, Canada

Spacious & Cozy Family Home in the Village of Chesterbr5 bedrooms, 2 & 1/2 baths, sleep’s 10 -14 adults and morebrbrWelcome to our family home located in the Village of Chester, with an abundance of charm and comfort.brbrA spacious open main floor with expansive windows, fireplace, lends itself to entertaining.brbrThis home has a relaxing atmosphere & is ready for you to enjoy a fabulous Chester holiday.brbrWell suited to accommodate large families & friends as the house can sleep to 10-14 adults & more.brbrSpacious & Cozy Family Home in the Heart of Chester Village – Sleeps 10-14br5 Bedrooms, 2.5 Bathrooms – Ideal for Large Groups, Families & FriendsbrbrWelcome to our spacious family home in the picturesque Village of Chester, where comfort meets charm. Whether you`re planning a family reunion, a getaway with friends, or just looking to relax, our home is the perfect retreat.brbrThe SpacebrThis 5-bedroom, 2.5-bathroom home is designed to accommodate large groups comfortably, offering space for 10-14 adults (or more) with room to spread out and enjoy each other`s company.brbrThe open-concept main floor boasts expansive windows that let in natural light, a cozy fireplace, and a generous layout perfect for entertaining. The fully equipped kitchen includes stainless steel appliances and a double oven, making meal prep a breeze. Gather around the dining table (which seats 10+, with extensions for larger groups) or relax in the comfortable living room featuring a propane fireplace and lovely views of the private backyard.brbrStep outside to enjoy the tranquil outdoor space with seating, dining areas, a propane BBQ, and a chiminea—perfect for a cozy evening under the stars. The relaxing atmosphere of our home makes it the ideal spot for a Chester holiday.brbrBedrooms & AccommodationsbrMain Floor:brbrMaster Suite: King-sized bed, en-suite bathroom with glass shower, and a walk-in closet.brSecond Bedroom: 2 Double beds.brThird Bedroom: Double bed.brAdditional Full Bathroom on this floor.brSecond Floor (Private Access via Stairwell):brbrFourth Bedroom: Queen-sized bed.brBasement:brbrFifth Bedroom: Queen-sized bed.brAdditional Sitting Area and pull-out couch that comfortably sleeps 2 more adults (Queen-sized).brLocationbrNestled on a quiet, residential street with mature trees and privacy-enhancing rhododendrons, our home is just a short walk from Chester`s charming shops, parks, and vibrant art and culture scene. Whether you`re looking to explore the local history, enjoy outdoor activities, or simply relax, you`ll find something for everyone.brbrWhy You’ll Love Our HomebrPerfect for large families, friends, or groups (10-14 adults + more).brA peaceful, family-friendly neighborhood with easy access to local attractions.brPrivate backyard with outdoor seating, BBQ, and a chiminea for relaxed evenings.brPet-friendly—bring your furry friends along to enjoy the village!brClose to parks, restaurants, art galleries, and outdoor adventures.brGuest AccessbrGuests will have full access to the entire home, including the private backyard and ample parking with space for up to six cars in the semi-circular driveway, plus plenty of street parking. Whether you`re here for a short stay or a longer visit, we want you to feel right at home!brbrIdeal for:brCouples seeking a peaceful getawaybrBusiness travelers looking for a comfortable home basebrFamilies with kids who need space to spread outbrLarge groups or friends reuniting for a fun tripbrPet-friendly for your furry companionsbrWe look forward to welcoming you and helping you create memories in our beloved Chester home. Book your stay now for a fabulous holiday!brbrMy place is close to art and culture and parks. You’ll love my place because of the location, the people, the outdoors space, the ambiance, and the neighbourhood. My place is good for couples, business travellers, families (with kids), big groups, and furry friends (pets).brbrWe like to give guests their space. brAvailable by email phone or text.brbrOur place is close to art and culture and parks. You’ll love our it because of the location, the outdoors space, the ambiance & the neighbourhood. Beauport is good for couples, business travellers, families, big groups, and furry friends (pets).br- Quiet Hours after 9pmbr- Pets may be allowed with approval from host for additional fee. Please inquire.br- check in is anytime after 4pm and before 9:00pm - Please advise and if you require a later check-in for approval.br- Check outs are any time before 10ambr-Hot tub on site is non operational and scheduled for removal and must not be used in any way at any timebr- Absolutely no partiesbr- refunds: 50% refund if cancelling more than 60 days from check in. no refunds for cancellations within 60 days of check in. brWe have a Strict No Parties or Events Allowed policy.brRefundable Damage Deposit applied to each stay.brGuests must sign external rental Agreement.brSmoking is NOT AllowedbrGUESTS MUST HAVE PREVIOUS POSITIVE REVIEWS
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Bath 4

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Sleep 14

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Exceptional(5)

$576.59

/ Nightly
Private Vacation Home

The Chester House. Seaside in the village, with private wharf

Chester, Nova Scotia, Canada

An acre on the ocean in Chester's front harbour, this historic gem was once The Lobster Plant dormitory. It has been lovingly revived to offer a cozy soulful getaway, including full access to a private wharf.brThis home is thoughtfully designed and curated by the owner, Suzanne.brWith 3 bedrooms accommodating up to 6 guests, a spacious living room, large chef's kitchen and a separate dining area, it's a perfect place to gather.brRelax indoors or enjoy the surround patio, a swim off the wharf, a game of croquet on the lawn, or a nap in the hammock chair.or a nap in the hammock chair.brbrThe house is located on a quiet road facing west over Chester's front harbour - an easy and beautiful 10 minute stroll around the harbour into the heart of the village.brbrChester is brimming with charm, sailing heritage and things to see and do. Explore the galleries and shops, check out the great restaurants, see a play, discover island beaches, hit the oceanside links, pamper yourself at the Sensea Spa or just kick back with a beverage and enjoy the view.brbrAlso, easily check out Halifax and the south shore sites of Mahone Bay and Lunenburg (all within 40 minutes).brbrDon't hesitate to reach out. We're here to help make your stay great! There is magic that drew us to this place and keeps us here.
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Exceptional(2)

$227.38

/ Nightly
Private Vacation Home

Tucked Away Treasure- Cozy 2 bed house, large yard and pets welcome!

Chester, Nova Scotia, Canada

Welcome to a quiet 2 bed 1.5 bath house tucked away on a dead end road. Only 40 minutes to HRM, close to magazine worthy destinations such as Chester, Mahone Bay and Lunenburg. The popular Sensea spa is 10 minutes away. Come and relax in nature with the large deck and lovely yard. This property is perfect for anyone that wants a respite from the busy city life, mature trees and wildlife on the property; deer, fox, pheasant, blue jays and robins for example help you ground and reset from modern day life.
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Sleep 4

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Exceptional(16)

$165.21

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Cottage

Seascape,Art Deco cottage

Chester, Nova Scotia, Canada

Two bedroom Art Deco cottage on 6 acre estate. Minutes from ocean and downtown amenities in the village of Chester. There are some great places to eat such as N.S.oldest pub The Focsile tavern, Kiwi Cafe and White's Gate fine dining. The village has some very unique shops such as Chez Glass, Light my fire and the Emporium shop. Also the village offers beauty salons, a bank and the famous Chester playhouse. On the other end of the road is the grocery store and n.s.liquor commission. Located 5 minutes away by car is the Chester golf course which has a fabulous restaurant and beautiful view of the islands and ocean. The cottage offers a fully equipped kitchen, T.V.,cable and Wi-Fi. Barbeque, lawn chairs provided. No pets and no smoking allowed. Priced per week $1200.00. (Closed from Dec.-May)
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Sleep 4

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$608.95

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Private Vacation Home

Chester Village Gem – Elegant Coastal Retreat Sleeps 6

Chester, Nova Scotia, Canada

Welcome to your perfect seaside escape in the heart of Chester, Nova Scotia. This newly renovated, beautifully appointed home was thoughtfully designed by a renowned interior designer to capture the essence of classic coastal living with a refined, traditional touch.brNestled in the charming village core, this 3-bedroom, 2.5-bathroom vacation rental offers breezy elegance just steps from Chester’s shops, cafés, galleries, and waterfront. Whether you're here to relax or explore, everything is within easy walking distance.brInside, enjoy a bright, open-concept living and dining area on the main floor, flowing effortlessly to a fully equipped kitchen featuring a premium WOLF range and all the essentials for home-cooked meals. The space opens onto a private rear patio—perfect for entertaining—with a propane BBQ and outdoor seating area.brUpstairs you'll find the primary suite offers a luxurious king bed, plush linens, and a spa-like ensuite with a deep soaker tub. Two additional queen bedrooms share a stylish full bathroom, with an extra powder room located on the main floor for guests. Crisp, soft linens and towels are provided, adding to the breezy beachside vibe throughout.brWith modern comforts like air conditioning, washer/dryer, and tasteful design touches at every turn, this home is the perfect blend of timeless Chester charm and contemporary luxury.brCome stay, unwind, and experience coastal living at its finest.
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Sleep 6

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Exceptional(25)

$470.09

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Private Vacation Home

Custom Built Home On The Scenic Waterfront Facing The Picturesque MarriottsCove

Chester, Nova Scotia, Canada

The main floor features a comfortably furnished, open concept Great Room, with sitting, kitchen and dining areas, as well as the master bedroom suite, a powder room and a separate study. Large windows across the front rooms give good views of the cove and make this a light, bright living space. brDownstairs there's an additional sitting area with walkout to the patio and garden, two more good-sized bedrooms and a full bathroom.br The custom-crafted kitchen has painted cabinets, quartz worktops, stainless steel appliances, a large island/breakfast bar and a pantry. brThree bedrooms: Master with Queen bed and flat screen TV; walk through closet leading to en-suite bathroom. Second bedroom with Queen bed; third with twin beds.brThree bathrooms: Master en-suite with shower and two sinks; bathroom downstairs with bath/shower; main floor powder room.brThe house is situated in a large, private lot with expansive lawn to the front and woodland to the rear.brA deck at the main living level extends the full width of the house. Doors from the Great Room lead out to a fully furnished seating and dining area, with barbecue; doors from the master bedroom lead out onto a furnished seating area. brAt the lower level there's direct access to the patio, lawn and gardens, from which it's just a short walk to the waterfront. brThe property backs onto the Chester Connection trail, for walking and cycling.
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Exceptional(36)

$377.72

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Cottage

Ahoy!...Oceanfront Family Cottage with Hot Tub, Near South Shore Attractions

Chester, Nova Scotia, Canada

Come and Relax at this private family cottage with direct waterfrontage and floating dock. This Nova Scotia cottage rental is conveniently located approximately 45 mins from Halifax and 55 mins from the Annapolis Valley. Three Sheeps to the Wind Cottage is located close to many restaurants and pubs in Chester (6mins) and Mahone Bay (10mins) by car. Historic Lunenburg (25mins) by car. The Sensea Nordic Spa is about 10mins away by car. brbrThis Nova Scotia cottage rental features air conditioning, wood stove and a hot tub. There are three bedrooms located on the second floor with two bedrooms featuring a queen size bed and the third bedroom has a twin over double bunk bed. The finished room in the walk out basement features a Murphy Wall Bed with real double mattress. There is a full bath with tub on second floor and powder room on main floor. brbrThere is one main floor patio with bbq with amazing water front views and gorgeous sunsets. There is a small deck off of master bedroom to enjoy your morning coffee. Three Sheeps to the Wind is the last home on a private road so it is quite private yet close to all amenities in nearby Chester and Mahone Bay.brbrThere is a public golf course and salt water pool in Chester, not to mention many unique shops. Mahone bay is the home of the three churches and more restaurants and shops. The historic UNESCO world heritage town of Lunenburg (home of the Bluenose Schooner) is close by and the famous Oak Island is located less then 5 mins by car and tours are offered.brbrSki Martock can found approximately (40km) away for winter downhill skiing and snowboarding and they offered groomed cross country ski trails as well.brbrThe 35 Km Chester Connector Trail is located less then 2 km from the cottage and has year round access for various activities.brbrPLEASE NOTE: Currency rates will sometimes default to U.S. Currency. The Detailed Pricing and Book it Now features, also quote is usually in U.S. currency totals. If you are a Canadian traveller, please select to see rates in Canadian funds or contact us directly for a quote in Canadian dollars. Prices are set and charged in Canadian funds. A $500CDN Security Deposit will collected by the owner on guests first arrival day.
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Sleep 7

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Exceptional(4)

$224.84

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Hotel Resort

Luxurious Escapes Await: Private Hot Tubs and Kayaks at Norse Geodesic Retreat

Chester, Nova Scotia, Canada

Welcome to a realm of pure luxury and serenity at Norse Geodesic Retreat. Our exquisite domes are the epitome of elegance, meticulously designed to offer an unparalleled escape from the ordinary. Step inside and immerse yourself in the embrace of opulence.brbrIndulge in the ultimate relaxation with your own private hot tub, nestled within the tranquil surroundings of nature. Unwind as warm, bubbling waters caress your senses, melting away the stresses of the day. Let the soothing jets rejuvenate your body and soul, creating an oasis of pure bliss.brbrFor those seeking adventure, venture to the nearby lake with our complimentary kayaks. Glide effortlessly across the glistening waters, surrounded by breathtaking scenery. Explore hidden coves, discover secluded beaches, and immerse yourself in the wonders of nature.brbrOur domes are a harmonious blend of luxury and nature, offering an escape like no other. Immerse yourself in the sumptuous comfort of a queen-size bed, awaken your senses in a full bathroom adorned with high-end amenities, and prepare culinary delights in a well-appointed kitchenette.brbrExperience the epitome of elegance, where every detail is thoughtfully curated to create an unforgettable stay. Whether you seek relaxation, adventure, or a harmonious blend of both, our luxurious domes at Norse Geodesic Retreat invite you to embark on a journey of indulgence and serenity.
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Sleep 3

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Exceptional(2)

$233.2

/ Nightly
Cottage

Indulge in luxurious bliss : private Hot Tub, kayaking. So much more

Chester, Nova Scotia, Canada

Welcome to our enchanting retreat at Norse Geodesic Retreat! Nestled amidst breathtaking natural beauty, our property offers a one-of-a-kind escape for those seeking tranquility and luxury. Immerse yourself in the comfort and elegance of our geodetic domes, thoughtfully designed to provide a serene sanctuary. Relax on your private deck or soak in the rejuvenating hot tub while marveling at the picturesque surroundings. Explore the nearby lake with convenient access for paddle boating or embark on nature trails for scenic hikes. Whether you're seeking a romantic getaway or a peaceful retreat, our property offers an unforgettable experience. Book your stay at Norse Geodesic Retreat and immerse yourself in the perfect blend of nature, relaxation, and indulgence.
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$188.19

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Private Vacation Home

ChesterGuestHouse · Charming Chester Classic in Village Core

Chester, Nova Scotia, Canada

Charming 3-Bedroom Classic Home in the Heart of Chester. Escape to this delightful two-story home, designed to offer a perfect blend of comfort and charm. Nestled in the vibrant center of Chester Village, you’ll have shops, restaurants, Chester Playhouse, and Yacht Club all right at your doorstep. Your ideal getaway awaits—book now and make this charming house your home base for discovering the magic of Chester!brThe spacebrBeautifully light-filled two-story home heritage home, offering comfort, convenience, and plenty of space for families or friends.brbrFeatures:br- Ground Floor: A separate office for remote work, a spacious living/dining area, a fully equipped kitchen with stainless steel appliances, a large den for relaxation, and an additional bathroom with a shower.brbr- Second Floor: Three well-appointed bedrooms—two with queen beds and one with a double bed—plus a modern bathroom with a shower.brbr- Location: Situated in a quiet, family-friendly neighborhood, perfect for those seeking a peaceful living environment. Fenced backyard.brbr- Parking: Driveway accommodates two vehicles.brThis home is ideal for anyone looking for a comfortable and quiet home in the middle of town.
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Home Most popular vacation rentals in Chester

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$936.34

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Private vacation home

White Cottage

Chester, Nova Scotia, Canada

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Bath 6

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Sleep 8

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$146.58

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Apartment

Seapearl Studio: Cozy Coastal Retreat in the Heart of Chester

Chester, Nova Scotia, Canada

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$165.21

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Cottage

Seascape,Art Deco cottage

Chester, Nova Scotia, Canada

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Sleep 4

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$224.84

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Hotel resort

\"Luxurious Escapes Await: Private Hot Tubs and Kayaks at Norse Geodesic Retreat\"

Chester, Nova Scotia, Canada

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Sleep 3

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$319.42

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Private vacation home

One 12 Queen

Chester, Nova Scotia, Canada

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Bath 2

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Sleep 6

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$377.72

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Cottage

Ahoy!...Oceanfront Family Cottage with Hot Tub, Near South Shore Attractions

Chester, Nova Scotia, Canada

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Bath 1

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Sleep 7

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$381.92

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Cabin

Cozy Oceanfront Escape with Hot Tub

Chester, Nova Scotia, Canada

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Sleep 4

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$453.40

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Private vacation home

Spacious Chester Home with Spectacular Ocean Views!

Chester, Nova Scotia, Canada

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Sleep 8

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$618.07

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Cottage

Superb Oceanfront with Optional Boathouse

Chester, Nova Scotia, Canada

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Bath 2

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Sleep 10

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$576.59

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Private vacation home

The Chester House. Seaside in the village, with private wharf

Chester, Nova Scotia, Canada

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Bath 1

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Sleep 6

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Most Popular Cities in Nova Scotia