Best Vacation Homes in Roxbury
House
10.0(6 Reviews)
2 Bedrooms
1 Bath
4 Guests
2500 ft²
Fireplace/Heating
Balcony/Terrace
Kitchen
Air Conditioner
US $518/Night
7 Nights - US $3,623
House
9.8(5 Reviews)
3 Bedrooms
2 Baths
6 Guests
1496.18 ft²
Spa- Fireplace/Heating
Pet Friendly
Parking
US $328/Night
7 Nights - US $2,298
Cabin
10.0(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $420/Night
7 Nights - US $2,939
Apartment
9.8(45 Reviews)
1 Bedroom
1 Bath
4 Guests
600 ft²
- Fireplace/Heating
- Balcony/Terrace
- Kitchen
- Parking
US $190/Night
7 Nights - US $1,331
House
2 Bedrooms
1 Bath
4 Guests
1200 ft²
Private Pool- Fireplace/Heating
Pool
Ocean View
US $1,152/Night
7 Nights - US $8,066
House
10.0(12 Reviews)
6 Bedrooms
4 Baths
12 Guests
4298 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,373/Night
7 Nights - US $9,611
House
10.0(8 Reviews)
7 Bedrooms
5 Baths
20 Guests
69965 ft²
- Private Pool
Hot Tub- Spa
- Fireplace/Heating
US $2,285/Night
7 Nights - US $15,997
House
10.0(5 Reviews)
3 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $702/Night
7 Nights - US $4,911
Roxbury Luxury Rentals
House
10.0(2 Reviews)
3 Bedrooms
3 Baths
8 Guests
2400 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Pet Friendly
US $1,533/Night
7 Nights - US $10,730
House
9.4(51 Reviews)
5 Bedrooms
4 Baths
12 Guests
3800 ft²
- Private Pool
- Hot Tub
- Spa
- Fireplace/Heating
US $1,405/Night
7 Nights - US $9,832
House
9.8(7 Reviews)
6 Bedrooms
3 Baths
12 Guests
3800 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,378/Night
7 Nights - US $9,644
House
10.0(2 Reviews)
5 Bedrooms
3 Baths
10 Guests
3000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,236/Night
7 Nights - US $8,653
House
9.4(9 Reviews)
4 Bedrooms
4 Baths
10 Guests
3100 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $1,204/Night
7 Nights - US $8,428
House
10.0(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
2050 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,195/Night
7 Nights - US $8,364
House
9.4(3 Reviews)
4 Bedrooms
2 Baths
8 Guests
2400 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $1,170/Night
7 Nights - US $8,187
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
10 Guests
2400 ft²
- Hot Tub
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $926/Night
7 Nights - US $6,481
Roxbury Pet Friendly Vacation Rentals
House
9.6(24 Reviews)
3 Bedrooms
1 Bath
6 Guests
1500 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $279/Night
7 Nights - US $1,950
House
10.0(1 Review)
3 Bedrooms
3 Baths
8 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $696/Night
7 Nights - US $4,870
House
3 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $156/Night
7 Nights - US $1,092
House
4.0(4 Reviews)
6 Bedrooms
5 Baths
12 Guests
3500 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
US $529/Night
7 Nights - US $3,703
House
3 Bedrooms
3 Baths
8 Guests
3100 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $961/Night
7 Nights - US $6,730
House
3 Bedrooms
2 Baths
6 Guests
- Balcony/Terrace
- Pet Friendly
- Kitchen
- Air Conditioner
US $90/Night
7 Nights - US $630
House
4 Bedrooms
4 Baths
8 Guests
- Hot Tub
- Spa
- Fireplace/Heating
- Pool
US $665/Night
7 Nights - US $4,658
Roxbury Large Vacation Homes
House
10.0(1 Review)
5 Bedrooms
3 Baths
6 Guests
3000 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Kitchen
US $588/Night
7 Nights - US $4,115
Why Choose Rent By Owner for your Roxbury 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 Roxbury
When should you plan your Vacation Rentals stay?
Choosing the optimal time to visit here can enhance your experience, as understanding seasonal patterns and climate conditions in Roxbury, Connecticut, USA, helps you find the best moments for booking your ideal vacation rental in this charming region.
Peak Season Highlights
Summer (June to August)
This is when the region experiences warm weather, making it ideal for outdoor activities and exploring the scenic beauty of the area. Booking your vacation rentals during this time ensures you enjoy the vibrant summer atmosphere.
Average Temperature Daytime: 75-85°F - Nighttime: 55-65°F
Fall (September to November)
During this season, the area transforms with beautiful fall foliage, offering a picturesque setting for your getaway. It’s a popular time to visit as many travelers seek to experience the stunning colors in this destination.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
Off-Season Highlights
Winter (December to February)
The quiet winter months bring cooler temperatures, providing a peaceful retreat away from the crowds. It’s an excellent time to enjoy cozy accommodations and serene surroundings in this region.
Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
Early Spring (March to May)
Before the summer rush, this is a slower period when nature begins to bloom. Visiting here during early spring offers a tranquil experience and the chance to enjoy the budding scenery without high demand.
Average Temperature Daytime: 50-60°F - Nighttime: 30-40°F
Weekly Weather Forecast for Roxbury
How to Book Your Roxbury 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 Roxbury
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 spacious patio or deck area to take in the scenic views of the region.
- Make use of private gardens or landscaped yards perfect for relaxing or outdoor activities.
- Take advantage of a fire pit or outdoor fireplace for cozy evenings under the stars.
- Utilize access to hiking trails or woodland areas directly from the property for exploring the nearby natural beauty.
- Relax by a seasonal outdoor pool, ideal for warm days spent outdoors in this destination.
- Benefit from ample parking space or drive-up access suitable for exploring the surrounding countryside.
- Experience outdoor recreational facilities such as a tennis court, volleyball area, or sports court often available at premium properties in the area.
Top Attractions Around Roxbury
What attractions are nearby?
In this charming region, you can enjoy outdoor activities such as hiking and exploring scenic trails, as well as discovering local parks and natural attractions that showcase the area's serene beauty.
Family Activities
- Roxbury Nature Trails: Explore scenic walking and hiking paths that offer family-friendly outdoor adventures immersed in the natural beauty of the region.
- Housatonic River Activities: Enjoy fishing, kayaking, or tubing along the calming waters of the river, perfect for a relaxing day with loved ones.
- Local Farms and Orchards: Visit nearby farms for seasonal fruit picking and farm tours, providing engaging experiences for children and adults alike.
- Community Events and Festivals: Participate in local gatherings and seasonal festivals that showcase the area's culture and bring families together in a welcoming setting.
Adult Activities
- Hiking at Roxbury Land Trust Trails: Explore scenic trails that showcase the natural beauty of this destination, perfect for outdoor enthusiasts seeking tranquil woodland walks.
- Fishing in Nearby Lakes: Spend your day relaxing by the water, enjoying the abundant fishing opportunities offered by the lakes in the region.
- Visiting Local Farms and Markets: Experience the region’s agricultural charm by browsing fresh produce and artisanal goods at local farms and markets.
- Golf at Area Courses: Play a round of golf at nearby courses designed to provide both leisure and challenge amid picturesque surroundings.
Roxbury Travel Tips
How Can You Make the Most of Your Stay?
- Explore local outdoor activities: Take advantage of the region's scenic parks and trails to enjoy hiking, biking, or simply unwinding in nature.
- Visit nearby attractions: Make time for visiting local points of interest that showcase the area's unique charm and history.
- Plan your stay around seasonal events: Check the calendar for festivals or community gatherings to enrich your experience here.
- Choose a well-located vacation rental: Select accommodations that offer easy access to the area's main attractions and natural beauty for a more convenient stay.
Transportation Options
- Connecticut Transit Bus Service: Offers convenient local transportation within the area, making it easy to explore this destination and its nearby attractions.
- Rental Cars: Provides flexible travel options for visitors looking to explore the region at their own pace, with numerous rental agencies available nearby.
- Taxi and Rideshare Services: Available throughout the area to offer quick and reliable transportation directly to your vacation rental or local points of interest.
- Private Shuttle Services: Suitable for groups or those seeking a comfortable transfer from regional airports directly to your stay here.
Local Customs Options
- Local Craftsmanship: You’ll notice that handcrafted items and artisanal goods are highly valued, reflecting the region’s appreciation for traditional skills and local artistry.
- Seasonal Celebrations: Participating in seasonal festivals and community events offers a glimpse into the area's cultural heritage and welcoming spirit.
- Historical Respect: Respect for historical sites and preservation efforts is a common custom, emphasizing the community's pride in its heritage.
- Outdoor Etiquette: When exploring the scenic outdoors, it’s customary to practice Leave No Trace principles, ensuring the natural beauty remains pristine for everyone to enjoy.
Roxbury Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Roxbury?
There are a lot of options in Roxbury. If you plan on staying in the Roxbury area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Roxbury:
- 1.5HrsNYC, Best Town, Restaurants, Shopping - Heated Pool PoshPadsCT "MOOSEHORN"
- Nature & Luxury @Lavender Lake Est (Kosher optional)
- Charming country home in Roxbury
- STUNNING Home on 3 acre Private Pond w. Hot Tub, BBQ, Firepit
- BEST Town Roxbury, Restaurants! PoshPadsCT 1.5 Hrs NYC,Heated Pool,Bikes,GasBBQ
- Secluded Architectural gem in the heart of Roxbury - Modern, Chic & Dreamy Pool
- Best Town ROXBURY, Restaurants - 1.5 Hrs NYC! PoshPadsCT 5BR, HeatedPool, GasBBQ
- Best Town within 1.5 Hrs NYC, Restaurants, Celebs, Shops,VIEWS! Hot Tub Spa, BBQ
- Roxbury Cabin Retreat
- Within a walking distance of hiking trails and a short drive to Lake Waramaug.
2. Which vacation homes in Roxbury are best for families?
If you are looking for a family-friendly vacation home in Roxbury, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Roxbury:
3. How many Rentbyowner vacation rentals are available in Roxbury?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 26 in the Roxbury 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 Roxbury.
4. What is the cancellation policy for vacation rentals in Roxbury, Connecticut?
Cancellation policies vary depending on the property owner and listing details. It's important to review the specific cancellation terms on the listing page or contact the host directly before booking.
5. Are there any specific check-in and check-out times I should be aware of when staying in this area?
Check-in and check-out times are set by each property owner. You can find these details listed with the property information, or you may contact the host for clarification to ensure a smooth arrival and departure.
6. How do I find a pet-friendly vacation rental in Roxbury, Connecticut?
To locate pet-friendly options, use the search filters available on the booking platform. Be sure to read the pet policy on the listing and communicate with the owner if you have any special requirements for your stay.
7. What amenities are typically included in vacation rentals here?
Most properties offer amenities such as Wi-Fi, parking, fully equipped kitchens, and outdoor spaces. The specifics will be listed on each property’s page, so reviewing these details helps ensure your needs are met.
8. How can I confirm the availability of a vacation rental during my travel dates?
Availability can be checked through the booking platform by selecting your desired dates. If you have questions about availability or need assistance, reaching out directly to the property owner is recommended for real-time confirmation.
