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

Home in Seabright
4.97 out of 5 average rating, 97 reviewsDome in the Woods
PedroRating, 5 starstoday
The place was very organized and welcoming. It had everything we could need, it was in a very clean condition, and very well equipped. There was a guide with things to do and places for food. One thing to keep in mind is that there is an open roof so id recommend bringing eye masks. It was fun watching the wild life out the window.
Guest favourite

Cabin in Lunenburg
4.98 out of 5 average rating, 48 reviewsLakefront Luxury Retreat
RuslanaRating, 5 stars3 weeks ago
We had a truly wonderful stay! Everything was exactly as described — peaceful, clean, and thoughtfully prepared. We especially appreciated the attention to detail — it’s clear that the hosts care deeply about their guests’ experience. The nature around the place is absolutely beautiful, and the quietness made it feel like a real retreat. Thank you for such a lovely atmosphere. We’d be happy to return someday!
Superhost

Home in Chester
4.9 out of 5 average rating, 10 reviewsEndeavour Cottage
ShelbyRating, 5 stars2 weeks ago
This was a fantastic place to stay as it was clean, thoughtfully equipped, and architecturally beautiful. My girlfriends and I booked the cottage for a cozy night in after a visit to the nearby Nordic spa, and it exceeded our expectations. The space was inviting with plenty of amenities that made our stay comfortable and relaxing. The only drawbacks were related to lighting. There were no lamps in the whole cottage, so we had to rely on the overhead lights, which made the atmosphere feel less cozy in the evening. Additionally, while the majority of the windows are not designed for curtains, it would have been nice to have some window coverings in the one bedroom downstairs where they could be hung to help block out the morning light. Overall, it was a wonderful experience, and we’d absolutely stay again.
Top guest favourite

Home in Chester
4.97 out of 5 average rating, 32 reviewsC’scape Cozy getaway Chester, Nova Scotia, Canada
SherriRating, 5 stars7 months ago
Perfect for couples or solo travelers. Walkable town and shopping. Spotless accommodations and beautiful decor. Looking forward to returning again!!
Top guest favourite

Home in Chester
4.97 out of 5 average rating, 33 reviewsHome in the Heart of Chester
RachelRating, 5 stars1 month ago
Beautiful home in the perfect location! We had everything we needed and were most comfortable! Bright and so well decorated! Our son was playing in a golf tournament which was very close by allowing us to come back and forth while we waited. Always enjoy visiting the pretty town of Chester!
Top guest favourite

Home in Chester
4.98 out of 5 average rating, 55 reviewsThe Whale House
LeeAnneRating, 5 stars1 week ago
Our stay at The Whale House was perfect! Located in the heart of Nova Scotia’s South Shore, this stunning home is a true treasure! It offers breathtaking views of a peaceful dock filled with boats and sailboats. Gretha was a fantastic host—her directions were clear, & her warm, flexible approach to check-in made us feel immediately at ease. Gretha was incredibly responsive & helpful throughout our stay, always just a message away. The home is immaculate & tastefully decorated with charming whale-themed accents. The cozy pillows & unique artwork add character & coastal charm. We loved the spacious kitchen, especially the oversized island where we enjoyed family meals and games. The large entryway, comfy beds, and thoughtful details made it feel like home. The location was ideal—close to beaches, waterside restaurants, shopping, & the famous Shore Club lobster supper. We woke each morning to the sound of song birds! We’re so grateful to Gretha for sharing her beautiful home with us.
Guest favourite

Tiny home in Chester Grant
4.92 out of 5 average rating, 79 reviewsLakefront tinyhome Chester Grant with hot tub
DanielleRating, 5 stars1 week ago
What a perfect getaway for my daughter and I for her prom weekend nights. So peaceful and serene I couldn’t have asked for a better location. The only thing I would say is the Wi-Fi wasn’t super great for us, but we have very old phones and we weren’t very much concerned about it either because we were away to get away not to be on Wi-Fi. Maybe it was working better if we had to try it more than a couple of times but we just threw our phones away and enjoyed what we had there. I highly recommend this place and I would definitely go back.
Guest favourite

Cottage in Riverport
4.95 out of 5 average rating, 42 reviewsA Dream Cottage in a Village by the Sea
DaliaRating, 5 stars6 days ago
We had a great time at the Point House. The house gave us panoramic views of the cove and pond. Hot tub a plus. Emma was very generous, friendly and welcoming.
Quick stats about holiday rentals in Chester
Total rentals
50 properties
Nightly prices starting at
₹5,192 before taxes and fees
Total number of reviews
1.2K reviews
Family-friendly rentals
40 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
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- Family-friendly rentals Chester
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- Cottage rentals Chester
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- Oak Island
- Cresent Beach
- Crescent Beach, Lunenburg County, Nova Scotia
- Halifax Citadel National Historic Site
- Atlantic Splash Adventure
- Rissers Beach Provincial Park
- Hirtle's Beach
- Cape Bay Beach
- Rainbow Haven Beach
- Bayswater Beach Provincial Park
- Point Pleasant Park
- Canadian Museum of Immigration at Pier 21
- Maritime Museum of the Atlantic
- Dauphinees Mill Lake
- Conrad's Beach
- Beach Meadows Beach
- Oxners Beach
- The Links at Brunello
- Halifax Public Gardens
- Halifax Central Library
- Lawrencetown Beach Provincial Park
- Hunts Point Beach
- Battery Point Beach
- Bracketts Beach