Best Vacation Homes in Weston
5706 ft²
8 Guests
4 Bedrooms
3 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
CA $1,568/Night
For 7 Nights CA $10,972
645.83 ft²
5 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Apartment
- Fireplace/Heating
- Parking
- Air Conditioner
CA $700/Night
For 7 Nights CA $4,896
4 Guests
2 Bedrooms
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Pet Friendly
- Kitchen
CA $589/Night
For 7 Nights CA $4,121
1399.31 ft²
3 Guests
2 Bedrooms
2 Bathrooms
Apartment
- Balcony/Terrace
- Pet Friendly
- Parking
CA $244/Night
For 7 Nights CA $1,710
6 Guests
2 Bedrooms
1 Bathroom
House
- Fireplace/Heating
- Air Conditioner
- Internet
CA $499/Night
For 7 Nights CA $3,495
6 Guests
2 Bedrooms
1 Bathroom
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $276/Night
For 7 Nights CA $1,930
1 Guest
1 Bedroom
1 Bathroom
Couples Retreat
House
- Private Pool
- Fireplace/Heating
- Pool
CA $131/Night
For 7 Nights CA $916
3 Guests
2 Bedrooms
2 Bathrooms
Ocean View
Cottage
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $234/Night
For 7 Nights CA $1,639
Weston Luxury Rentals
10 Guests
5 Bedrooms
6 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
CA $3,977/Night
For 7 Nights CA $27,836
4750 ft²
13 Guests
5 Bedrooms
4 Bathrooms
Family Friendly
House
- Hot Tub
- Fireplace/Heating
- Pool
CA $2,889/Night
For 7 Nights CA $20,226
4300 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Ocean View
House
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $2,216/Night
For 7 Nights CA $15,515
12 Guests
6 Bedrooms
5 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
CA $2,133/Night
For 7 Nights CA $14,932
15 Guests
9 Bedrooms
8 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $2,072/Night
For 7 Nights CA $14,505
6550 ft²
12 Guests
6 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $2,008/Night
For 7 Nights CA $14,054
6400 ft²
12 Guests
6 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $1,962/Night
For 7 Nights CA $13,736
4300 ft²
8 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Hot Tub
CA $1,789/Night
For 7 Nights CA $12,524
Weston Pet Friendly Vacation Rentals
4700 ft²
9 Guests
5 Bedrooms
4 Bathrooms
Ocean View
House
- Private Pool
- Fireplace/Heating
- Pool
CA $975/Night
For 7 Nights CA $6,825
3100 ft²
7 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $774/Night
For 7 Nights CA $5,419
6 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pet Friendly
- Kitchen
CA $710/Night
For 7 Nights CA $4,967
6 Guests
4 Bedrooms
2 Bathrooms
Pet Friendly
House
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
CA $1,368/Night
For 7 Nights CA $9,576
500 ft²
2 Guests
1 Bedroom
1 Bathroom
Ocean View
Apartment
- Oceanfront
- Fireplace/Heating
- Ocean View
CA $181/Night
For 7 Nights CA $1,269
800 ft²
3 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $317/Night
For 7 Nights CA $2,215
500 ft²
2 Guests
1 Bedroom
1 Bathroom
Family Friendly
Cottage
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
CA $229/Night
For 7 Nights CA $1,605
4 Guests
2 Bedrooms
3 Bathrooms
Ocean View
Condo
- Fireplace/Heating
- Pool
- Ocean View
CA $570/Night
For 7 Nights CA $3,991
Weston Large Vacation Homes
10 Guests
5 Bedrooms
3 Bathrooms
Group Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
CA $1,177/Night
For 7 Nights CA $8,242
9 Guests
5 Bedrooms
6 Bathrooms
Ocean View
House
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
CA $1,525/Night
For 7 Nights CA $10,675
6 Guests
6 Bedrooms
6 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Air Conditioner
- Internet
CA $1,481/Night
For 7 Nights CA $10,367
10 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Pet Friendly
- Kitchen
- Air Conditioner
CA $597/Night
For 7 Nights CA $4,176
10000 ft²
10 Guests
5 Bedrooms
6 Bathrooms
Family Friendly
House
- Balcony/Terrace
- Kitchen
- Air Conditioner
CA $597/Night
For 7 Nights CA $4,176
17 Guests
7 Bedrooms
9 Bathrooms
Ocean View
House
- Private Pool
- Hot Tub
- Fireplace/Heating
CA $3,023/Night
For 7 Nights CA $21,161
Why Choose Rent By Owner for your Weston 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 Weston
When should you plan your Vacation Rentals stay?
Choosing the right time to visit here can enhance your experience, as each season offers unique opportunities to enjoy the local charm and serene surroundings of this destination in Connecticut.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this period, you can enjoy pleasant weather and longer daylight hours, making it ideal for exploring the scenic surroundings of the area.
Average Temperature Daytime: 70°F to 80°F - Nighttime: 50°F to 60°F
Early Fall (September to October)
This time of year offers mild temperatures and vibrant foliage, providing a picturesque backdrop for your stay in this destination.
Average Temperature Daytime: 65°F to 75°F - Nighttime: 45°F to 55°F
Off-Season Highlights
Winter (December to February)
The colder months bring quieter surroundings and fewer tourists, making it a peaceful time to experience the region's tranquility.
Average Temperature Daytime: 30°F to 40°F - Nighttime: 20°F to 30°F
Late Fall to Early Winter (November)
As the leaves fall and temperatures drop, this season offers a serene atmosphere for those seeking a quieter escape in this part of Connecticut.
Average Temperature Daytime: 50°F to 60°F - Nighttime: 35°F to 45°F
Weekly Weather Forecast for Weston
How to Book Your Weston 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 Weston
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 a private outdoor swimming pool to relax and unwind during your stay.
- Take advantage of spacious patios or decks ideal for outdoor dining or gathering with friends and family.
- Experience the beauty of well-maintained gardens and lush lawns surrounding your accommodation.
- Make the most of outdoor fire pits perfect for cozy evenings under the stars.
- Benefit from access to scenic walking paths or nature trails nearby for outdoor exploration.
- Utilize outdoor barbecue grills to prepare delicious meals while enjoying the fresh air.
- Appreciate the availability of private yards or fenced outdoor spaces for children or pets to play safely.
Top Attractions Around Weston
What attractions are nearby?
While staying here, you'll find the area offers a variety of outdoor activities and scenic spots to explore, making it an ideal destination for those looking to enjoy nature and local attractions nearby.
Family Activities
- Weston Recreation Center: Engage your family in a variety of indoor and outdoor activities designed for all ages at the local recreation center, making it a perfect spot for fun and fitness.
- Silvermine Arts Center: Explore creative workshops, art exhibits, and performances that inspire family members to appreciate and participate in the arts within this cultural hub of the area.
- Weston Town Beach: Spend a relaxing day by the water at this scenic beach, ideal for swimming, picnicking, and building sandcastles with your loved ones during your stay here.
- Weston Historical Society Museum: Discover the region's history through interactive exhibits and family-friendly programs that provide educational entertainment for children and adults alike.
Adult Activities
- Visit the Weston Historical Society Museum: Explore the area's rich history through engaging exhibits that provide insights into local heritage.
- Enjoy outdoor activities at Devil's Den Preserve: Experience serene walking trails and scenic views ideal for nature lovers seeking tranquility in this region.
- Play a round of golf at Cannon Ridge Golf Course: Take advantage of this well-maintained course for a relaxing day of golfing close to your stay.
- Discover nearby lakes and waterways: Engage in kayaking, fishing, or simply unwinding at the peaceful lakes that are perfect for outdoor recreation here.
Other Places to Stay in Weston, CT
Lucius Pond Ordway / Devil's Den Preserve
Weston Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Dining Options: Take advantage of the region’s diverse culinary scene to enjoy memorable meals during your stay.
- Visit Outdoor Spaces: Make the most of the area's natural beauty by spending time at parks and scenic spots nearby.
- Plan Cultural Activities: Engage with local arts and community events to experience the authentic charm of the destination.
- Book Ahead for Popular Attractions: Secure your preferred vacation rentals early to ensure a comfortable and convenient stay in this inviting locale.
Transportation Options
- Weston Train Station: This station offers convenient regional train services that connect you to nearby cities and facilitate easy travel through the area.
- Interstate 95: A major highway providing quick access to surrounding towns and attractions, making road trips around the region straightforward and efficient.
- Local Bus Services: Local bus routes operate within the vicinity, offering an affordable way to explore this destination without the need for a car rental.
- Private Shuttle Services: Several private shuttle options are available to help you reach popular destinations and airports nearby with comfort and ease.
Local Customs Options
- Traditional Cherry Blossom Festivals: In the area, celebrating cherry blossoms is a cherished custom that brings the community together each spring, offering an authentic cultural experience during your stay.
- Farmers' Market Gatherings: Local markets in this destination highlight fresh, regional produce and crafts, providing a glimpse into the region’s agricultural heritage and vibrant local economy.
- Seasonal Holiday Celebrations: Throughout the year, seasonal events like harvest festivals and winter holiday parades reflect the area's rich community spirit and festive traditions.
- Preservation of Historic Sites: Respect for historical landmarks is evident here, with many locals valuing the preservation of their heritage and inviting visitors to appreciate the region's cultural roots.
Frequently Asked Questions About Weston?
1. What are the top vacation rentals in Weston?
There are a lot of options in Weston. If you plan on staying in the Weston area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Weston:
- Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
- Spacious 5-bedroom house with waterfall view and walk to town
- Interior Designer's Enchanting Home with Private Beach 1.5hrs from Brooklyn
- Summer getaway with Pool and Fully stocked Chef's Kitchen
- Charming Historic Connecticut Home W/Spacious Yard
- Luxury Coastal Estate, 7min to NYC train & beach. Heated pool & amazing gardens
- Designer Treehouse with Spa Bath
- Charming 3-bedroom Ranch in Weston Near Westport & Fairfield
- Cozy, fully renovated 2BR home with a barn in peaceful Weston, CT for relaxation
- Modern 4 bed 4.5 bath w hot tub & heated pool close to beach
2. Which vacation homes in Weston are best for families?
If you are looking for a family-friendly vacation home in Weston, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Weston:
3. How many Rentbyowner vacation rentals are available in Weston?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 52 in the Weston 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 Weston.
4. What is the cancellation policy for vacation rentals in Weston, Connecticut?
The cancellation policy varies by property; you should review the specific listing details or contact the owner directly to understand the terms and any applicable fees.
5. Are there any additional fees or charges I should be aware of when booking a vacation rental in this area?
Additional fees such as cleaning, service charges, or security deposits are typically outlined in the listing. It's recommended to review these details carefully or reach out to the host for clarification.
6. How do I secure my reservation at a vacation rental here?
Reservations can be secured through the booking platform by following the instructions provided on the listing page. Confirming availability and completing the payment process will ensure your booking is confirmed.
7. What amenities are commonly included in vacation rentals in Weston, Connecticut?
Many properties offer amenities like Wi-Fi, parking, kitchen facilities, and outdoor spaces. Specific amenities are listed on each property’s page, so it’s best to review those details before booking.
8. What should I know about check-in and check-out procedures for vacation rentals in this region?
Check-in and check-out times vary by property and are specified in the listing. Contact the owner if you need special arrangements or have questions about arrival and departure procedures.
Weston Top Rated Vacation Rentals
1800 ft²
8 Guests
3 Bedrooms
2 Bathrooms
Family Friendly
Other
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $420/Night
For 7 Nights CA $2,940
2000 ft²
6 Guests
3 Bedrooms
2 Bathrooms
Ocean View
House
- Private Pool
- Oceanfront
- Fireplace/Heating
CA $1,360/Night
For 7 Nights CA $9,521
5200 ft²
8 Guests
4 Bedrooms
4 Bathrooms
Family Friendly
Cabin
- Private Pool
- Pool
- Balcony/Terrace
CA $1,970/Night
For 7 Nights CA $13,788
8 Guests
4 Bedrooms
3 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Kitchen
CA $1,323/Night
For 7 Nights CA $9,262
2200 ft²
5 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Pool
- Balcony/Terrace
CA $1,092/Night
For 7 Nights CA $7,644
8 Guests
4 Bedrooms
2 Bathrooms
Family Friendly
House
- Fireplace/Heating
- Pool
- Balcony/Terrace
CA $655/Night
For 7 Nights CA $4,584
1380 ft²
6 Guests
3 Bedrooms
3 Bathrooms
Ocean View
Cottage
- Private Pool
- Fireplace/Heating
- Pool
CA $487/Night
For 7 Nights CA $3,407
3100 ft²
4 Guests
3 Bedrooms
3 Bathrooms
Family Friendly
House
- Private Pool
- Fireplace/Heating
- Pool
CA $393/Night
For 7 Nights CA $2,748
