Chester Vacation Homes

A large, two-story house with a steeply pitched roof and a chimney.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chester holiday homes

A modern living room with a flat-screen TV, a fireplace, a sofa set, and a large window with blinds.

1. Cozy 3-Bedroom, 2-Bath Home with Private Pool & Hot Tub, Chester Front Harbour

Chester

A view of a waterfront property with a dock and a small building.

2. Oceanfront Luxury Magical Views Sunset and Sunrise

Western Shore

Cynthia K G.

HK$2,032 total

includes taxes & fees

29 Nov - 30 Nov

A wooden cabin and a geodesic dome structure with seating and a fire pit, surrounded by a forest.

3. Pet-Friendly Glamping Dome close to Peggy’s Cove!

Seabright

Judy

HK$1,989 total

includes taxes & fees

6 Nov - 7 Nov

A cozy living room with a grey sofa, a white coffee table, and a wooden ceiling.

4. Oceanview 3-Bedroom Cottage | Fireplace | Sauna | Near Halifax

Boutiliers Point

Joanna

HK$1,643 total

includes taxes & fees

6 Nov - 7 Nov

A bedroom with a bed, bedside tables, a chair, a desk, a dresser, and a ceiling fan.

5. Pretty Bachelor with Balcony near River & Trails

Bridgewater

HK$1,050 total

includes taxes & fees

7 Nov - 8 Nov

View all properties

Find holiday rentals that suit your style

Cottages

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Chester Hotel Reviews

The Homeport Motel

10/10 Excellent

"It was queit and quite cozy. Amazing night sleep!"

Days Inn & Conference Center by Wyndham Bridgewater

8/10 Good

"The room and amenities in the room were good, breakfast was good/sufficient, and restaurant was quaint. Gym on the other hand could definitely use some upgrades/additions. Although people probably aren’t spending a lot of time in the gym there, a decent machine for weights and/or some free weights. That’s really my only criticism for this place."

Oceanfront Cottage on a Quiet Cove Just Outside Lunenburg

10/10 Excellent

"We loved every moment of our stay at the cottage! It is located perfectly- close to town but secluded enough that you feel you’re in your own little cove. Sitting outside you can enjoy pure silence, which is hard to come by these days. The provided s’mores package was a hit! We also enjoyed using the kayaks and exploring the area on the water. Despite being chilly out, we were still able to take advantage of all the outdoor amenities. Since we came at the start of the off season, many shops and restaurants in town were closed for the season, but that made town a lot less busy, which we enjoyed! The price of the cottage was very reasonable. We do plan on coming back in swimming season!"

The Dockside Inn & Restaurant

10/10 Excellent

"We had a wonderful room facing the harbor on the second floor. Fairly quiet because of the season but the view was wonderful--also helped that we had beautiful fall weather. Staff was excellent. They offered to let us use their washer and dryers when they were done with their daily needs when we inquired about doing a laundry. We chose to use a laundromat on outskirts of town where we were able to drop off and pick up later in day. Let us explore Lundenburg and its great selections of Victorian houses and the fishery museum. The restaurant while not fancy had a good selection of dishes. Would stay there again"

Find out more about Chester