We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Chester Vacation Rentals

List your property
Owner log in
Check in
— / — / —
Check out
— / — / —
Guests
0+ rooms, 2+ guests
Distance from
1 mi
Price per night
$0
$1,000+
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
Neighborhood
50 rentals in Chester.
Sort by:
Tripadvisor Sort
Chester Garden House, 4 + Bedrooms, 2.5 Baths, vacation rental in Chester

Chester Garden House, 4 + Bedrooms, 2.5 Baths

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Delightful self contained cottage in the Charming Village of Chester by the sea, vacation rental in Chester

Delightful self contained cottage in the Charming Village of Chester by the sea

1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
East Coast Glamping Inc. Luxury camping holidays in Nova Scotia, vacation rental in Chester

East Coast Glamping Inc. Luxury camping holidays in Nova Scotia

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection
Serenity, vacation rental in Chester

Serenity

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Sandy Cove Exclusive, vacation rental in Chester

Sandy Cove Exclusive

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Stoneybrook House -- Historic Property on 1.7 Acres of Land, vacation rental in Chester

Stoneybrook House -- Historic Property on 1.7 Acres of Land

6 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Breath taking Ocean Harbour Front 3 Bedroom 2 Bath, vacation rental in Chester

Breath taking Ocean Harbour Front 3 Bedroom 2 Bath

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
5 bedroom quiet and spacious retreat, vacation rental in Chester

5 bedroom quiet and spacious retreat

5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Check in
Check out
Payment Protection
60 Foot Lap Pool - Steps to Ocean - 5 min walk to town, vacation rental in Chester

60 Foot Lap Pool - Steps to Ocean - 5 min walk to town

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Historic Home in the Heart of Chester Nova Scotia, vacation rental in Chester

Historic Home in the Heart of Chester Nova Scotia

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
Save time - get the best Chester rentals sent straight to your email!
A-Frame - located in Chester, vacation rental in Chester

A-Frame - located in Chester

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Carriage House, vacation rental in Chester

Carriage House

2 bedrooms
4 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
Hubbards/Halifax Oceanfront Home in Nova Scotia, vacation rental in Chester

Hubbards/Halifax Oceanfront Home in Nova Scotia

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Spectacular Oceanfront Living in Authentic Fishing Village, vacation rental in Chester

Spectacular Oceanfront Living in Authentic Fishing Village

6 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
On the Beautiful South Shore Near Chester and Hubbards, Ns, vacation rental in Chester

On the Beautiful South Shore Near Chester and Hubbards, Ns

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Cooperage Cottage - Peaceful & Family Friendly, Oceanfront, vacation rental in Chester

Cooperage Cottage - Peaceful & Family Friendly, Oceanfront

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
The Little House in Hubbards - a  private heritage house steps from the sea, vacation rental in Chester

The Little House in Hubbards - a private heritage house steps from the sea

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
The White Cape on the Cove - A year round oceanside retreat, vacation rental in Chester

The White Cape on the Cove - A year round oceanside retreat

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Oceanfront Elegant Home with Games Room On Picturesque Big Tancook Island, vacation rental in Chester

Oceanfront Elegant Home with Games Room On Picturesque Big Tancook Island

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Mahone Bay's great place to stay, read our reviews, vacation rental in Chester

Mahone Bay's great place to stay, read our reviews

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
This elegant,cosy seaside home with breathtaking ocean views, can sleep six., vacation rental in Chester

This elegant,cosy seaside home with breathtaking ocean views, can sleep six.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Tranquility And Beauty At This Tucked  Away Home ~ Right On The Ocean!, vacation rental in Chester

Tranquility And Beauty At This Tucked Away Home ~ Right On The Ocean!

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Ocean Front Retreat!, vacation rental in Chester

Ocean Front Retreat!

2 bedrooms
1 bathroom
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Amazing Ocean-view just steps to Fox Point Beach!, vacation rental in Chester

Amazing Ocean-view just steps to Fox Point Beach!

2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
CUSTOM LUNENBURG 2BR HOME WITH PRIVATE HILLTOP SETTING, BEACH AND PATHWAY., vacation rental in Chester

CUSTOM LUNENBURG 2BR HOME WITH PRIVATE HILLTOP SETTING, BEACH AND PATHWAY.

2 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Sophisticated Condo, vacation rental in Chester

Sophisticated Condo

2 bedrooms
2 bathrooms
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Oceanfront Air Conditioned Boat House - One of a Kind! With Water Access., vacation rental in Chester

Oceanfront Air Conditioned Boat House - One of a Kind! With Water Access.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Cherry Lane Cottage Mahone Bay NS, vacation rental in Chester

Cherry Lane Cottage Mahone Bay NS

2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
River Ridge Lodge (B&B) - Beautiful Large 2 Bedroom w/Ensuite Bath, vacation rental in Chester

River Ridge Lodge (B&B) - Beautiful Large 2 Bedroom w/Ensuite Bath

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
White Cape on the Cove - Year round ocean retreat!, vacation rental in Chester

White Cape on the Cove - Year round ocean retreat!

4 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Check in
Check out
Payment Protection
Ice House Cottage, vacation rental in Chester

Ice House Cottage

1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
Check in
Check out
Payment Protection
The Breathtaking Foxpoint Wharf, vacation rental in Chester

The Breathtaking Foxpoint Wharf

3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
The Millett House... ocean front property on peaceful Indian Point..., vacation rental in Chester

The Millett House... ocean front property on peaceful Indian Point...

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
River Ridge Lodge (B&B) - Beautiful Queen Bedroom w/Ensuite Bath on 2nd Floor, vacation rental in Chester

River Ridge Lodge (B&B) - Beautiful Queen Bedroom w/Ensuite Bath on 2nd Floor

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Halifax, Nova Scotia Oceanfront Vacation Rental, vacation rental in Chester

Halifax, Nova Scotia Oceanfront Vacation Rental

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
Icicle, vacation rental in Chester

Icicle

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Check in
Check out
Payment Protection
Executive Ocean Front Estate with View of Waters of Mahone Bay, vacation rental in Chester

Executive Ocean Front Estate with View of Waters of Mahone Bay

5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check in
Check out
Payment Protection
Amazing Ocean-view just steps to Fox Point Beach!, vacation rental in Chester

Amazing Ocean-view just steps to Fox Point Beach!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check in
Check out
Payment Protection
Oceanside Retreat  Hubbards Nova Scotia, vacation rental in Chester

Oceanside Retreat Hubbards Nova Scotia

1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
The Lodge at Strum Island - A Private Island Paradise with a Club Ambiance, vacation rental in Chester

The Lodge at Strum Island - A Private Island Paradise with a Club Ambiance

6 bedrooms
7 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
River Ridge Lodge (B&B) - Beautiful Queen Bedroom w/Ensuite Bath on 1st Floor, vacation rental in Chester

River Ridge Lodge (B&B) - Beautiful Queen Bedroom w/Ensuite Bath on 1st Floor

1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Modern Oceanview Vacation Living In Deep Cove, vacation rental in Chester

Modern Oceanview Vacation Living In Deep Cove

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Ocean Retreat Hubbards N.S., vacation rental in Chester

Ocean Retreat Hubbards N.S.

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Long Hill Roost, Mahone Bay view apartment., vacation rental in Chester

Long Hill Roost, Mahone Bay view apartment.

2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
The Hull House - A sleeping giant tucked away in an ocean cove, vacation rental in Chester

The Hull House - A sleeping giant tucked away in an ocean cove

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
SUN, SAND, OCEAN in Hubbards Nova Scotia, vacation rental in Chester

SUN, SAND, OCEAN in Hubbards Nova Scotia

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
SUN, SAND, OCEAN, in Hubbards. What more do you need?, vacation rental in Chester

SUN, SAND, OCEAN, in Hubbards. What more do you need?

2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
The Cozy Clam Cottage~ Spectacular Views ~Best location for all your adventures, vacation rental in Chester

The Cozy Clam Cottage~ Spectacular Views ~Best location for all your adventures

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
Old Fish Store with a wharf, Mill Cove, Light House Route, Aspatogan, vacation rental in Chester

Old Fish Store with a wharf, Mill Cove, Light House Route, Aspatogan

3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
More info
Check in
Check out
Payment Protection

Quiet, Peaceful, Private Country Home on Large Area of Land

0 bedrooms
0 bathrooms
Sleeps 0
Match: Sleeps
More info
Vrbo.com logo
Check in
Check out
PreviousNext
1