5 Best Vacation Rentals in Chester - Holiday Lettings - Cabins

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56 Vacation rentals

(2) Excellent 

27

Vacation home with golf nearby in Chester

Southwest Nova Scotia / Chester

5 14 min stay varies

  • 5 bedrooms
  • sleeps 14
  • min stay varies
  • Child friendly
  • Pet friendly
  • Private garden
Elegant & Cozy Family Cottage in the Village of Chester 5 bedrooms, 2 & 1/2 baths, sleep’s 10 -13 adults Located inn the Village of Chester, with an abundance of charm and comfort. A spacious open main floor with expansive windows, fireplace, lends itself to entertain …see more

from $315 / night

$1,718 - $4,008 / week

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avg. 30 minutes

from $315 / night

19

Home accommodation in Chester

Southwest Nova Scotia / Chester

5 10 3 nights min

  • 5 bedrooms
  • sleeps 10
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Three storey historical home features traditional character and charm. Located in the historic seaside village of Chester. The House sleeps 10 people - 3 queen beds, and 2 single beds and a set of single bunk beds which are in the connecting room off one of the queen …see more

from $344 / night

$2,405 / week

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avg. 1 hour 57 minutes

from $344 / night

20

Chester Vacation cottage rental

Southwest Nova Scotia / Chester

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Ask about children
  • Ask about pets
RENTAL DESCRIPTION: In one of the historic homes of Lunenburg, a door gives way to a surprising find. Upstairs is an inviting, creatively designed and spacious loft style 1 bedroom 1 bath accommodation, that is upbeat with unique flourish, original art and maximum comfo …see more

from $97 / night

$679 / week

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from $97 / night

(3) Very Good 

34

Vacation condo in Chester

Southwest Nova Scotia / Chester

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 1 mi
  • Child friendly
  • Pet friendly
Breath taking Harbour Front 3 Bedroom 2 Bath Condo. Located on historic Chester Front Harbour. Private steps to the crystal clean water perfect for swimming in the summer months .The perfect mix. Master bedroom custom on suite with rain shower, walk in closet Recently …see more

from $173 / night

$1,209 / week

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from $173 / night

(9) Excellent 

Certificate of Excellence

16

Chester Vacation cottage rental

Southwest Nova Scotia / Chester

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Child friendly
Come to beautiful Chester and Stay in this Storybook 1600 Sq ft Cottage. It sits on a meticulously landscaped 2 acres overlooking the Coveside Stable. This cottage has all of the ammenities of home and is less than 5 minutes to the village of Chester, well known to sail …see more

Certificate of Excellence

from $172 / night

$1,203 / week

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Responds fast!
avg. 28 minutes

from $172 / night

7

Chester Vacation guest house rental

Southwest Nova Scotia / Chester

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Pet friendly
This 200-year-old carriage house is Chester’s hidden gem. Completely renovated by a renowned East Coast architect, this property is the perfect place to relax and get away. It is located in the heart of the Chester village, within walking distance from restaurants, Nova …see more

from $216 / night

$1,166 / week

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from $216 / night

13

Vacation cottage in Chester

Southwest Nova Scotia / Chester

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Ask about children
  • Ask about pets
RENTAL DESCRIPTION: Take in as much beauty as the undeveloped Nova Scotia waterfront has to offer, from this charming, private 2-story home. Located at the end of a winding private drive, this cape-style shingled cottage is sequestered in a pristine and natural setting …see more

from $162 / night

$1,131 / week

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from $162 / night

19

Chester Vacation cottage rental

Southwest Nova Scotia / Chester

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Ask about children
  • Ask about pets
RENTAL DESCRIPTION: This delightful single level bungalow cottage is nestled on Nova Scotia's amazing South Shore area of Green Bay. Here, you are directly across from a pristine white sand beach and close to Risser's Beach Provincial Park. Wake up to the sounds of the …see more

from $113 / night

$792 - $943 / week

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from $113 / night

(3) Very Good 

16

Vacation cottage in Chester

Southwest Nova Scotia / Chester

6 10 7 nights min

  • 6 bedrooms
  • sleeps 10
  • 7 nights min
  • Ask about children
  • Ask about pets
RENTAL DESCRIPTION: The locals say that Nova Scotia is the place where heaven meets earth, and nowhere is that more true than on this Peggy's Cove area oceanfront retreat. To see this 5 Bedroom 3.5 bath newly restored home and its picture-perfect sheltered cove, is to f …see more

from $237 / night

$1,659 - $1,885 / week

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from $237 / night

Great rentals within 20 miles that match your search

Distance approx 9.44 miles from Chester

10

Vacation cottage in Hubbards

Halifax Region / Hubbards

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Child friendly
Located right on the water. Only three steps off the deck to the beach. One of the last working fishing villages on St Margarets Bay. Fishing, swimming, biking, kayaking. Internet bbq tv close to restaurants and cafes. Lobster dinners at the local Hubbards Beach …see more

from $151 / night

$864 / week

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from $151 / night

Distance approx 6.63 miles from Chester

29

Home rental in Blandford

Southwest Nova Scotia / Blandford

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Nearest beach 6 mi
  • Child friendly
Welcome to a fully renovated four bedroom three bathroom two story Cape Cod home on the cove. Enjoy the views of the ocean from within this newly appointed retreat. Watch the sailboats and fishing boats while you soak up the sun either on the flat pebble beach out front …see more

from $169 / night

$1,230 - $1,593 / week

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from $169 / night

Distance approx 14.93 miles from Chester

10

Indian Harbour Vacation guest house rental

Halifax Region / Indian Harbour

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 10 mi
  • Child friendly
  • Private garden
This custom-built 3 floor oceanfront guest house is situated on a very private 2-acre property with 2 other cottages. It is located 4 km from one of Nova Scotia's top tourist attractions, Peggy's Cove, and it is 45 minutes from Halifax, the capital of Nova Scotia, and 1 …see more

from $126 / night

$876 - $1,209 / week

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from $126 / night

Distance approx 15.17 miles from Chester

(5) Excellent 

14

Lunenburg Vacation cottage accommodation

Southwest Nova Scotia / Lunenburg

4 8 5 nights min

  • 4 bedrooms
  • sleeps 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
This country cottage is situated in the quaint village of Feltzen South over looking the beautiful Lunenburg Bay. Occasionally catching glimpses of the Bluenose sailing in all of its magnificence, or enjoying the view from the deck, allow the sound of the ocean to rela …see more

from $216 / night

$1,511 / week

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from $216 / night

Distance approx 4.96 miles from Chester

26

Western Shore Vacation home rental

Southwest Nova Scotia / Western Shore

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Nearest beach 25 mi
  • Child friendly
  • Air conditioning
This home is situated on a peninsula and boasts ocean views from every window. Located on a quiet cove you can enjoy your own small beach area and clear views of the famous Oak Island. In the summer months the cove fills with sailboats and kayakers. Wake up in the morni …see more

from $259 / night

$1,813 / week

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avg. 1 hour 32 minutes

from $259 / night

Distance approx 15.2 miles from Chester

(1) Excellent 

7

Vacation cottage in Peggy's Cove

Halifax Region / Peggy's Cove

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
Unbeatable panoramic views! You can’t get closer to the ocean than Bluefin. Truly stunning views through the 8 foot patio door and from the deck – just 20... feet from waves lapping against ancient granite. There is no better way to start your day than with a coffee, fr …see more

from $169 / night

$1,010 / week

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Responds fast!
avg. 46 minutes

from $169 / night

Distance approx 9.65 miles from Chester

(4) Excellent 

12

Vacation cottage in Mahone Bay

Southwest Nova Scotia / Mahone Bay

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 25 mi
  • Child friendly
Cozy 2 storey cottage on a narrow, quiet lane in the heart of pictureque, tranquil Mahone Bay, Nova Scotia. Within walking distance to downtown, the waterfront, restaurants, bistros, coffee shops, pub, shopping, waterfront festivals and events. Fully equipped kitchen, …see more

from $164 / night

$777 / week

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avg. 1 hour 47 minutes

from $164 / night

Distance approx 11.95 miles from Chester

(3) Excellent 

9

Vacation home rental

Southwest Nova Scotia / Lunenburg

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Private garden
Very comfortable 2 bedroom bungalow with hardwood floors throughout. All new sofas, mattresses, linens, pillows, appliances etc. Very well equipped kitchen Both bathrooms recently updated Large lot with a backyard deck and new BBQ providing excellent views of the back …see more

from $87 / night

$605 - $950 / week

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Responds fast!
avg. 59 minutes

from $87 / night

Distance approx 15.49 miles from Chester

(12) Excellent 

Certificate of Excellence

15

Boutiliers Point Vacation cottage rental

Halifax Region / Boutiliers Point

5 min stay varies

  • sleeps 5
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Ocean, beach, privacy. You can have it all in our very spacious, open concept, modernized 'home away from home' that sits right on the water's edge on beautiful St Margarets Bay. Relax, tan, swim, snorkel, watch the birds or boats go by to in the summer or just relax …see more

Certificate of Excellence

from $173 / night

$1,207 / week

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Responds fast!
avg. 1 hour 41 minutes

from $173 / night

Distance approx 15.2 miles from Chester

(1) Excellent 

9

Vacation cottage in Peggy's Cove

Halifax Region / Peggy's Cove

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
Lighthouse Lane Cottages is set on a spectacular property overlooking St Margarets Bay. Oyster Cottage has amazing sea views and is literally steps from the Ocean. Tastefully decorated and well equipped this is the perfect spot to unwind and drink in the fresh salty air …see more

from $199 / night

$1,192 / week

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avg. 46 minutes

from $199 / night

Distance approx 19.66 miles from Chester

(1) Excellent 

20

Home rental in Riverport

Southwest Nova Scotia / Riverport

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Private garden
This four-bedroom home sits on a hill overlooking beautiful Hirtle's beach, Romkey Pond and the Atlantic Ocean. It is a short walk to the beach up the road and through the fields, or an easy drive for those who prefer to not to walk. Described as "a nature enthusiast's …see more

from $344 / night

$2,061 / week

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from $344 / night

Distance approx 18.34 miles from Chester

(5) Excellent 

11

Vacation home in Tantallon

Halifax Region / Tantallon

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Nearest beach 22 mi
  • Child friendly
  • Private garden
Beautiful Ocean Front Home nestled in St. Margarets Bay, Nova Scotia. Blue Heron is a newly renovated, four season, waterfront home located in beautiful St.Margarets Bay. Enjoy a Memorable summer vacation or a Romantic fall/winter getaway at the seashore. Enjoy your p …see more

from $195 / night

$1,295 / week

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avg. 2 hours 59 minutes

from $195 / night

Distance approx 16.51 miles from Chester

(4) Excellent 

13

Vacation cottage in Bridgewater

Southwest Nova Scotia / Bridgewater

1 3 1 night min

  • 1 bedroom
  • sleeps 3
  • 1 night min
  • Nearest beach 24 mi
  • Child friendly
  • Private garden
We are located in Beautiful Lunenburg County on the Salt Water Shores of Dayspring. This Private Cabin is nestled on the owner’s property overlooking the water with a private deck. Cabin Features: Rustic Nautical Décor with Wood Floors, Queen Bed and Single Cot, Kitche …see more

from $91 / night

$635 / week

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avg. 2 hours 13 minutes

from $91 / night

Distance approx 9.87 miles from Chester

14

Vacation cottage rental

Halifax Region / Hubbards

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
Studio Cottage located 250 feet from St Margaret's Bay. Cottage is in a historical building dating back to 1861 and has a 60" deck on two sides over looking the ocean. The building was once home to a General store, Post office and a Toy shop. The interior is set up like …see more

from $117 / night

$734 / week

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avg. 1 hour 22 minutes

from $117 / night

Distance approx 9.4 miles from Chester

(10) Excellent 

28

Vacation cottage in Hubbards

Halifax Region / Hubbards

3 7 nights min

  • sleeps 3
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Ask about children
Breath-taking ocean views from this studio sized, self contained, winterized cottage! Stunning sunrises over the bay will grab your heart with the sheer beauty of one of nature's wonders. Situated on the shoreline, this road provides 2.8 KMS of very picturesque walking. …see more

from $97 / night

$674 - $885 / week

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avg. 1 hour 14 minutes

from $97 / night

Distance approx 4.62 miles from Chester Show on Map

(5) Excellent 

22

Vacation cottage in Mahone Bay

Southwest Nova Scotia / Mahone Bay

1 3 3 nights min

  • 1 bedroom
  • sleeps 3
  • 3 nights min
  • Nearest beach 25 mi
  • Child friendly
  • Air conditioning
Far Far Away is a Canada Select 4 Star guesthouse located directly between Chester and Mahone Bay; a ten minute drive in either direction and 25 minutes to the UNESCO World Heritage Town of Lunenburg. The guest house shares a driveway with an early 1900s home and has oo …see more

from $130 / night

$907 / week

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avg. 1 hour 32 minutes

from $130 / night

Distance approx 9.43 miles from Chester

13

Hubbards Vacation home rental

Halifax Region / Hubbards

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
This home has been totally renovated, main floor has full kitchen, dining room, 3 chesterfields, 2 bedrooms, a full bathroom and laundry facilities. The house is designed to have a two family set up, with a separated unit consisting of one bedroom, bathroom, full kitche …see more

from $182 / night

$1,269 / week

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avg. 16 minutes

from $182 / night

Distance approx 15.2 miles from Chester

6

Cottage rental in Peggy's Cove

Halifax Region / Peggy's Cove

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly
Enjoy fantastic views of Clifty Cove and St Margaret’s Bay from the 8-foot patio door and deck. Sunfish Cottage is open-plan with a well-equipped kitchen. Super comfortable queen bed + a Double Simmons BeautyRest pull out sofa, 3-piece bathroom with shower, Sound of the …see more

from $169 / night

$1,010 / week

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avg. 46 minutes

from $169 / night

Distance approx 12.54 miles from Chester

21

Vacation boathouse in Queensland

Halifax Region / Queensland

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Child friendly
  • Pet friendly
  • Private garden
1,200 Sq foot bungalow with 75 feet of ocean frontage. Only a five minute walk from Queensland beach. Sea Salt Beach House has two bed rooms, as well as a queen sized sofa bed, sleep six comfortably here all while enjoying the vibrant community of Hubbards, conveniently …see more

from $287 / night

$2,004 / week

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from $287 / night

Distance approx 4.61 miles from Chester Show on Map

(1) Very Good 

17

Vacation home in Western Shore

Southwest Nova Scotia / Western Shore

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Nearest beach 25 mi
  • Child friendly
  • Air conditioning
Over The Way Cottage offers pet-friendly accommodations in Martin's Point, Nova Scotia. It's conveniently located between Mahone Bay and Chester. Close to local attractions but out of the way enough to feel like a rural retreat. Originally built in the early 1900s, by t …see more

from $156 / night

$1,088 / week

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avg. 1 hour 32 minutes

from $156 / night

Distance approx 18.24 miles from Chester

(10) Very Good 

20

Rose Bay Vacation cottage rental

Southwest Nova Scotia / Rose Bay

3 6 2 nights min

  • 3 bedrooms
  • sleeps 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
This 3 bedroom waterfront cottage is privately located at the end of a lane on a quiet cove of Rose Bay. The cottage sits on a landscaped two acre lot with an open and private view of the Bay. It is situated 100 feet off the water with a small shale/sand beach in front …see more

from $302 / night

$1,295 - $1,537 / week

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from $302 / night

Distance approx 19.52 miles from Chester

(16) Excellent 

33

Vacation home in Lunenburg

Southwest Nova Scotia / Lunenburg

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
"Gladee's at Hirtle's Beach" is a fourth generation, 150 year old home, anchored amidst a magnificent vista of ocean,lakes and glacial drumlin, considered by many to be Nova Scotia at its finest. The Creasers are well-respected for their restoration and transformati …see more

from $130 / night

$864 - $1,554 / week

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from $130 / night

Distance approx 9.87 miles from Chester

(1) Excellent 

15

Vacation cottage rental

Halifax Region / Hubbards

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Private garden
Ice House Cottage (Cottage #1) is a stone's throw from the waters edge; close to numerous sandy beaches, within minutes of Freewheeling Adventures, for kayaking and biking. Conveniently located just 8 minutes from Hubbards, and less than an hour from the communities of …see more

from $139 / night

$950 / week

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avg. 1 hour 22 minutes

from $139 / night

Distance approx 18.6 miles from Chester

(1)  

8

Lunenburg Vacation cottage rental

Southwest Nova Scotia / Lunenburg

1 4 1 night min

  • 1 bedroom
  • sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
Formery the post office/ general store for this small fishing community, now a comfortable cottage practically on the ocean. 4 acres to roam on, pebble beaches, woodland trails. Located close to the LaHave Bakery, ferryboat to Lunenburg and Mahone Bay, sand beaches - C …see more

from $132 / night

$831 / week

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from $132 / night

Distance approx 16.18 miles from Chester

(5) Excellent 

18

Vacation apartment in Glen Margaret

Halifax Region / Glen Margaret

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 16 mi
  • Ask about children
Private loft style studio apartment, located in scenic St. Margaret's Bay on the Lighthouse Route. Located on the sheltered Long Cove. Stunning ocean views from all windows and from the elevated wrap around deck which faces the waterfront. Walk down to the beach area an …see more

from $108 / night

$691 / week

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avg. 2 hours 39 minutes

from $108 / night

Distance approx 10.56 miles from Chester

10

Vacation home with swimming pool in Halifax

Halifax Region / Halifax

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
A house for those who want the best vacation home that money can provide. This beautiful, non-smoking home is centrally located in Hubbards, Nova Scotia, an easy 30-minute ride to the ancient Halifax fortifications, Peggy's Cove preservation district, and beautiful Mah …see more

from $581 / night

$4,065 / week

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from $581 / night

Distance approx 11.25 miles from Chester

(4) Excellent 

43

Vacation home in Lunenburg

Southwest Nova Scotia / Lunenburg

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Nearest beach 5 mi
  • Private garden
This charming two bedroom cottage sits on 2 acres of peaceful and private grounds bordered by mature trees and forest, with stunning unobstructed views of ocean, pasture and forest. Located on Second Peninsula, ( between the towns of Lunenburg and Mahone Bay) this lush …see more

from $143 / night

$1,058 / week

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Responds fast!
avg. 2 hours 8 minutes

from $143 / night

Distance approx 12.04 miles from Chester

(4) Excellent 

Certificate of Excellence

12

Lunenburg Vacation home rental

Southwest Nova Scotia / Lunenburg

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 5 mi
  • Child friendly
  • Pet friendly
We are now accepting summer 2019 reservations A well appointed and equipped 3 bedroom house ideally located in Lunenburg to be close to everything the town and area has to offer. We have a double deep private lot, private parking, small backyard deck, cute front porch …see more

Certificate of Excellence

from $87 / night

$864 - $1,122 / week

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Responds fast!
avg. 59 minutes

from $87 / night

Distance approx 12.23 miles from Chester

23

Vacation home in Lunenburg

Southwest Nova Scotia / Lunenburg

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Child friendly
  • Pet friendly
Built in 1874 by Shipbuilder Edward Conrad, this designated UNESCO World Heritage Site home is located in downtown Lunenburg directly overlooking the harbour. With the home's central location you will be able to walk to all the shops, restaurants, cafes, museums, banks, …see more

from $389 / night

$1,295 - $2,417 / week

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from $389 / night

Distance approx 8.82 miles from Chester

23

Vacation home in Mahone Bay

Southwest Nova Scotia / Mahone Bay

5 10 min stay varies

  • 5 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 7 mi
  • Child friendly
Beautiful seaside ‘Lunenburg Bump’ house, just a few minutes from the Town of Mahone Bay. Five Oaks sleeps 10 comfortably so it’s perfect for family gatherings. The house is twenty five years young and built to replicate a traditional 1700’s Cape house with Lunenburg Bu …see more

from $372 / night

$2,840 / week

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from $372 / night

Distance approx 11.24 miles from Chester

26

Lunenburg Vacation home rental

Southwest Nova Scotia / Lunenburg

4 8 2 nights min

  • 4 bedrooms
  • sleeps 8
  • 2 nights min
  • Nearest beach 20 mi
  • Child friendly
  • Air conditioning
Nestled on the South Shore of Nova Scotia on lovely Heckman’s Island. Just a few minutes drive to the Historic Town of Lunenburg, artists, photographers and kayakers alike will be delighted with the undeniable natural beauty of Blue Rocks. Blue Rocks is still a working …see more

from $146 / night

$1,021 / week

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from $146 / night