Best Vacation Homes in Canterbury
Cottage
10.0(16 Reviews)
1 Bedroom
1 Bath
2 Guests
Fireplace/Heating
Pet Friendly
Parking
Air Conditioner
US $230/Night
7 Nights - US $1,610
Apartment
10.0(4 Reviews)
4 Bedrooms
2 Baths
11 Guests
1001.04 ft²
Balcony/Terrace
View- Pet Friendly
- Parking
US $528/Night
7 Nights - US $3,694
Bed & Breakfast
9.8(94 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
Pool- Balcony/Terrace
Breakfast
US $232/Night
7 Nights - US $1,624
House
10.0(3 Reviews)
2 Bedrooms
1 Bath
7 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
Internet
US $220/Night
7 Nights - US $1,543
House
10.0(4 Reviews)
5 Bedrooms
4 Baths
10 Guests
4133.34 ft²
- Fireplace/Heating
- View
- Parking
- Internet
US $491/Night
7 Nights - US $3,439
House
9.8(9 Reviews)
1 Bedroom
1 Bath
4 Guests
1000 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
Kitchen
US $173/Night
7 Nights - US $1,208
Other
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $321/Night
7 Nights - US $2,247
New
Apartment
10.0(1 Review)
3 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $211/Night
7 Nights - US $1,477
Canterbury Luxury Rentals
House
5 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Pool
- Kitchen
- Parking
US $2,288/Night
7 Nights - US $16,013
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
US $1,084/Night
7 Nights - US $7,590
House
9.0(12 Reviews)
4 Bedrooms
2 Baths
16 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $973/Night
7 Nights - US $6,811
House
9.2(38 Reviews)
10 Bedrooms
4 Baths
14 Guests
5000 ft²
Private Pool
Hot Tub- Fireplace/Heating
- Pool
US $891/Night
7 Nights - US $6,239
House
9.8(17 Reviews)
7 Bedrooms
3 Baths
14 Guests
5000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $885/Night
7 Nights - US $6,197
House
8.8(6 Reviews)
9 Bedrooms
4 Baths
16 Guests
4000 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $781/Night
7 Nights - US $5,466
Other
10.0(24 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $727/Night
7 Nights - US $5,090
Other
10.0(4 Reviews)
5 Bedrooms
1 Bath
11 Guests
3336 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $700/Night
7 Nights - US $4,897
Canterbury Pet Friendly Vacation Rentals
House
10.0(11 Reviews)
4 Bedrooms
2 Baths
8 Guests
1500 ft²
- Hot Tub
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $423/Night
7 Nights - US $2,962
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
1506.95 ft²
Spa
Skiing- Fireplace/Heating
- View
US $257/Night
7 Nights - US $1,801
Cottage
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $426/Night
7 Nights - US $2,981
Cottage
9.6(39 Reviews)
3 Bedrooms
1 Bath
8 Guests
1502 ft²
- Skiing
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
US $380/Night
7 Nights - US $2,661
Apartment
8.0(1 Review)
4 Bedrooms
2 Baths
8 Guests
22604.21 ft²
- View
- Pet Friendly
- Parking
- Air Conditioner
US $326/Night
7 Nights - US $2,282
House
4 Bedrooms
2 Baths
7 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $474/Night
7 Nights - US $3,321
House
3 Bedrooms
1 Bath
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $344/Night
7 Nights - US $2,407
House
10.0(16 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $194/Night
7 Nights - US $1,360
Canterbury Large Vacation Homes
House
10.0(6 Reviews)
5 Bedrooms
3 Baths
7 Guests
- Hot Tub
- Fireplace/Heating
Ocean View- Balcony/Terrace
US $658/Night
7 Nights - US $4,604
Apartment
10.0(1 Review)
4 Bedrooms
2 Baths
10 Guests
2098.96 ft²
- Fireplace/Heating
- View
- Parking
- Internet
US $333/Night
7 Nights - US $2,329
House
7.4(3 Reviews)
4 Bedrooms
2 Baths
12 Guests
2100 ft²
- Fireplace/Heating
- Kitchen
- Parking
- Air Conditioner
US $470/Night
7 Nights - US $3,292
House
7 Bedrooms
7 Baths
14 Guests
5500.36 ft²
- Parking
- Internet
- Child Friendly
Wheelchair Accessible
US $584/Night
7 Nights - US $4,088
House
9.6(18 Reviews)
4 Bedrooms
2 Baths
10 Guests
3800 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $671/Night
7 Nights - US $4,696
House
9.2(57 Reviews)
5 Bedrooms
3 Baths
10 Guests
4132 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $505/Night
7 Nights - US $3,532
House
8.8(6 Reviews)
5 Bedrooms
2 Baths
12 Guests
2100 ft²
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $571/Night
7 Nights - US $3,997
House
8.4(14 Reviews)
5 Bedrooms
2 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $632/Night
7 Nights - US $4,421
Why Choose Rent By Owner for your Canterbury Vacation Rental Homes?
What makes our Vacation Rentals special?
Verified Listings
Book with confidence knowing every property meets our quality and safety standards.
Unbeatable Value
Enjoy competitive pricing with no hidden fees, providing exceptional value for every stay.
Diverse Options
From cozy cabins to luxurious villas, find a rental that suits your style and needs.
Best Times to Visit Canterbury
When should you plan your Vacation Rentals stay?
Choosing the ideal time to visit ensures you can enjoy the region's natural beauty and serene surroundings to the fullest when booking your perfect vacation rentals here.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this period, you can enjoy pleasant weather and vibrant natural scenery, making it an ideal time to explore the area. The region experiences warm days perfect for outdoor activities while accommodation rates are often higher due to increased visitor demand.
Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
Early Fall (September to October)
This season offers stunning fall foliage and mild temperatures, attracting visitors seeking a picturesque escape. Expect higher occupancy and premium prices in your chosen vacation rental here during these months.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
Off-Season Highlights
Winter (December to February)
The winter months bring cooler weather and fewer tourists, providing a quieter experience whether you're seeking solitude or planning budget-friendly stays. Booking here during winter ensures more availability and potentially better rates.
Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
Late Fall (November)
As the region transitions into colder weather, visitor numbers decrease, making it a good time for those looking to avoid crowds. This off-peak period also often features more affordable rates on vacation rentals.
Average Temperature Daytime: 50-60°F - Nighttime: 30-40°F
Weekly Weather Forecast for Canterbury
How to Book Your Canterbury Vacation Rental Home
What's our booking process?
Our platform allows you to browse a curated selection of vacation rentals. Once you find the ideal property, you’ll be redirected to a trusted booking partner to complete your reservation securely.
Booking Steps
01
Search Properties
Use our filters to find the right property that fits your needs.
02
Select a Rental
Click on your preferred listing to view details, amenities, and pricing.
03
Book Online
Follow the link to finalize your reservation directly on the partner’s website.
Explore and book the perfect rental in Canterbury
Common Vacation Rentals Amenities
What amenities can you expect?
Our Vacation Rentals are designed to offer all the comforts of home, often with added perks to make your stay unforgettable. Here’s some common amenities to look forward to:
Indoor Features
- Fully-equipped kitchens with modern appliances
- Comfortable living areas with flat-screen TVs
- Free Wi-Fi for staying connected
- Air conditioning and heating for year-round comfort
- In-unit washers and dryers for convenience
- Luxurious bedrooms with premium bedding
- Spa-like bathrooms with soaking tubs or walk-in showers
Outdoor Amenities
- Enjoy outdoor dining with a fully equipped patio or picnic area in your Canterbury accommodation.
- Relax by a private or shared outdoor fire pit to unwind after exploring the region.
- Take advantage of scenic walking or hiking trails surrounding your vacation rental.
- Make the most of spacious yards perfect for outdoor games and family activities.
- Benefit from easy access to local parks and natural reserves for outdoor recreation.
- Stay active with amenities like a swimming pool, either private or communal, available on some properties.
- Experience the beauty of the area's natural landscape with outdoor seating or lounging areas to enjoy the fresh air.
Top Attractions Around Canterbury
What attractions are nearby?
In this charming area, you'll find a variety of outdoor activities and local attractions nearby to enhance your stay, making it an ideal destination for exploring the natural beauty and cultural sites that Connecticut has to offer.
Family Activities
- Canterbury Green: Enjoy a family picnic or leisurely stroll in this scenic park, perfect for relaxing days outdoors.
- Bradley Playhouse: Experience local culture and entertainment with family-friendly performances at this historic theater nearby.
- Connecticut Civil War State Park: Visit this educational site to explore history through interactive exhibits and outdoor tours suitable for all ages.
- Mystic Seaport Museum: Take a short trip to learn about maritime history and explore historic ships, offering engaging activities for children and parents alike.
Adult Activities
- Visit the Canterbury Green:** Enjoy a relaxing stroll or picnic at this charming town green, perfect for unwinding and experiencing local community life.
- Explore the Joshua's Tract Conservation Land:** Discover scenic trails and nature views in this peaceful preserve, ideal for hiking and birdwatching in the region.
- Experience local art at the Canterbury Historical Society Museum:** Dive into the area's rich history and artistic heritage through engaging exhibits and collections.
- Attend seasonal events and festivals:** Participate in lively community celebrations that showcase the region’s cultural traditions and local flavors throughout the year.
Other Places to Stay in Canterbury, CT
Haul of Fame Museum
Prudence Crandall Museum
Canterbury Green
Canterbury Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Events and Festivals: Take advantage of seasonal events to immerse yourself in the area's vibrant community spirit during your stay.
- Visit Scenic Outdoor Spots: Discover nearby parks, trails, and natural attractions to enjoy the region's picturesque landscapes firsthand.
- Plan Your Dining Experience: Sample regional cuisine at local eateries to get a true taste of what makes this destination unique.
- Utilize Convenient Transportation Options: Make use of available transit services or rental bikes to easily access key locations around here.
Transportation Options
- Canterbury Shuttle Service: This reliable transportation option offers convenient rides within the area, making it easy for you to explore local attractions and amenities.
- Connecticut Transit Buses: Public bus services connect Canterbury to nearby towns and cities, providing an affordable and eco-friendly way to travel around the region.
- Rental Car Services: Numerous rental agencies operate in the area, giving you the flexibility to explore Canterbury and its surroundings at your own pace.
- Taxi and Ride-Sharing Options: Taxis and ride-sharing services are readily available here, offering quick and direct transportation when you need to get around efficiently.
Local Customs Options
- Traditional American Celebrations: Join local festivities during holidays like Independence Day, where community gatherings and fireworks showcase the area's patriotic spirit.
- Farmers' Market Etiquette: Support regional agriculture by browsing at farmers' markets with a respect for local customs, including fresh produce sampling and engaging with vendors.
- Religious Community Events: Experience the region’s welcoming atmosphere through various church festivals and events that highlight local traditions and hospitality.
- Seasonal Outdoor Activities: Embrace the local appreciation for nature by participating in seasonal outdoor pursuits such as leaf peeping or small-town recreational gatherings.
Canterbury Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Canterbury?
There are a lot of options in Canterbury. If you plan on staying in the Canterbury area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Canterbury:
- Spectacular waterfront cottage on the most beautiful lake in CT's 'Quiet Corner'
- The Cabin on Pachaug Pond
- Hanover Vineyards
- A fun filled,family friendly, farmhouse home, rural,but close to all amenities
- Barn Stay at Hanover Vineyards
- Cozy 1-bedroom cottage with WiFi, AC in charming Windham
- A Lot Like Paradise. Quiet. Peaceful. Cozy. Spacious.
- Romantic, Historic 1750 Early Colonial House near Casinos, Spa, Mystic and more!
- New Lake House w/Game Room & Stunning Views
- 4-bedroom house in Windham - Pet Friendly - Thread City Family Escape
2. How many vacation rentals have private pools in Canterbury?
There are 6 vacation rentals with private pools near Canterbury. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Canterbury are best for families?
If you are looking for a family-friendly vacation home in Canterbury, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Canterbury:
4. How many Rentbyowner vacation rentals are available in Canterbury?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 151 in the Canterbury area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Canterbury.
5. What is the cancellation policy for vacation rentals in Canterbury, Connecticut?
Cancellation policies vary by property, so it is important to review the specific listing details or contact the owner directly for information regarding refunds and cancellation deadlines.
6. Are there any additional fees I should be aware of when booking a vacation rental in the area?
Additional fees such as cleaning charges, service fees, or security deposits may apply. Always check the listing details or communicate with the host for a comprehensive understanding of all costs involved.
7. How do I find out about amenities available at a rental in Canterbury, CT?
Amenities are typically listed on the property page; however, for specific questions or to confirm availability, reaching out to the property owner can ensure you have accurate and up-to-date information.
8. What is the process for checking in and out of vacation rentals here?
Check-in and check-out procedures are outlined in each listing, but it’s recommended to contact the host beforehand to confirm arrival times and any special instructions to ensure a smooth experience.
9. How can I ensure my preferred dates are available at a rental here?
Availability calendars are usually shown on the listing page; for confirmed reservation or to inquire about flexible dates, contacting the property owner directly is advised.
Canterbury Top Rated Vacation Rentals
Other
10.0(18 Reviews)
4 Bedrooms
2 Baths
8 Guests
2800 ft²
- Fireplace/Heating
- Pool
- Ocean View
- Balcony/Terrace
US $466/Night
7 Nights - US $3,260
Apartment
10.0(2 Reviews)
1 Bedroom
1 Bath
4 Guests
1100 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $217/Night
7 Nights - US $1,521
Apartment
9.8(30 Reviews)
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $232/Night
7 Nights - US $1,622
Cottage
9.6(20 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $302/Night
7 Nights - US $2,117
US $107/Night
7 Nights - US $746
Hotel
8.1(402 Reviews)
1 Bath
247.57 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Parking
US $101/Night
7 Nights - US $707
US $134/Night
7 Nights - US $937
Hotel
7.8(1125 Reviews)
1 Bath
- Pool
- Breakfast
- Kitchen
- Parking
US $101/Night
7 Nights - US $704
