Best Vacation Homes in Wilton
Cottage
9.6(7 Reviews)
1 Bedroom
1 Bath
6 Guests
950 ft²
Fireplace/Heating
Ocean View
Balcony/Terrace
View
US $311/Night
7 Nights - US $2,175
House
6.0(1 Review)
1 Bedroom
1 Bath
6 Guests
947.22 ft²
Oceanfront- Fireplace/Heating
- Ocean View
- View
US $319/Night
7 Nights - US $2,233
Bed & Breakfast
9.8(54 Reviews)
1 Bedroom
1 Bath
- Fireplace/Heating
- Balcony/Terrace
Breakfast
Kitchen
US $430/Night
7 Nights - US $3,009
Cottage
9.4(46 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Fireplace/Heating
Pet Friendly- Kitchen
Parking
US $253/Night
7 Nights - US $1,769
Apartment
5.5(2 Reviews)
2 Bedrooms
2 Baths
4 Guests
247.57 ft²
- Pet Friendly
- Parking
Air Conditioner
Internet
US $206/Night
7 Nights - US $1,439
House
10.0(15 Reviews)
2 Bedrooms
2 Baths
4 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $519/Night
7 Nights - US $3,635
Cottage
10.0(14 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $441/Night
7 Nights - US $3,086
Cottage
10.0(4 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $490/Night
7 Nights - US $3,427
Wilton Luxury Rentals
House
5 Bedrooms
6 Baths
10 Guests
Hot Tub- Fireplace/Heating
Pool- Kitchen
US $2,913/Night
7 Nights - US $20,392
House
6 Bedrooms
6 Baths
14 Guests
- Hot Tub
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $2,013/Night
7 Nights - US $14,088
House
10.0(5 Reviews)
5 Bedrooms
4 Baths
15 Guests
Private Pool- Hot Tub
- Fireplace/Heating
- Pool
US $1,792/Night
7 Nights - US $12,545
House
10.0(41 Reviews)
6 Bedrooms
5 Baths
10 Guests
4500 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,744/Night
7 Nights - US $12,209
House
10.0(2 Reviews)
4 Bedrooms
4 Baths
8 Guests
4300 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $1,624/Night
7 Nights - US $11,366
House
6 Bedrooms
5 Baths
12 Guests
- Fireplace/Heating
- Pet Friendly
- Kitchen
- Parking
US $1,563/Night
7 Nights - US $10,939
House
10.0(1 Review)
9 Bedrooms
8 Baths
15 Guests
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,518/Night
7 Nights - US $10,626
House
6 Bedrooms
4 Baths
12 Guests
6550 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,438/Night
7 Nights - US $10,063
Wilton Pet Friendly Vacation Rentals
Cottage
2 Bedrooms
2 Baths
3 Guests
- Oceanfront
- Fireplace/Heating
- Ocean View
- View
US $129/Night
7 Nights - US $903
Apartment
2 Bedrooms
2 Baths
3 Guests
1399.31 ft²
- Balcony/Terrace
- Pet Friendly
- Parking
- Air Conditioner
US $179/Night
7 Nights - US $1,253
Apartment
1 Bedroom
1 Bath
2 Guests
- Fireplace/Heating
- Pet Friendly
- Air Conditioner
- Internet
US $166/Night
7 Nights - US $1,159
House
10.0(17 Reviews)
3 Bedrooms
2 Baths
9 Guests
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $982/Night
7 Nights - US $6,875
Hotel
8.6(39 Reviews)
9 Baths
314.55 ft²
- Fireplace/Heating
- Balcony/Terrace
- View
- Breakfast
US $322/Night
7 Nights - US $2,254
House
10.0(4 Reviews)
4 Bedrooms
3 Baths
7 Guests
3100 ft²
- Fireplace/Heating
- Balcony/Terrace
- Pet Friendly
- Kitchen
US $596/Night
7 Nights - US $4,169
House
10.0(2 Reviews)
5 Bedrooms
4 Baths
9 Guests
4700 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Ocean View
US $920/Night
7 Nights - US $6,438
House
10.0(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Hot Tub
- Fireplace/Heating
- Ocean View
US $875/Night
7 Nights - US $6,124
Wilton Large Vacation Homes
House
10.0(9 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Fireplace/Heating
- Air Conditioner
- Internet
Child Friendly
US $863/Night
7 Nights - US $6,038
House
10.0(8 Reviews)
5 Bedrooms
3 Baths
10 Guests
4400 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $1,291/Night
7 Nights - US $9,039
House
9.8(14 Reviews)
5 Bedrooms
2 Baths
8 Guests
2000 ft²
- Oceanfront
- Hot Tub
Spa- Fireplace/Heating
US $816/Night
7 Nights - US $5,714
House
9.8(6 Reviews)
5 Bedrooms
4 Baths
8 Guests
4300 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Fireplace/Heating
US $1,434/Night
7 Nights - US $10,037
House
6 Bedrooms
4 Baths
12 Guests
6400 ft²
- Private Pool
- Hot Tub
- Fireplace/Heating
- Pool
US $1,438/Night
7 Nights - US $10,063
Villa
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Fireplace/Heating
- Pet Friendly
- Kitchen
US $1,416/Night
7 Nights - US $9,913
House
3 Bedrooms
2 Baths
10 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,169/Night
7 Nights - US $8,184
House
6 Bedrooms
5 Baths
10 Guests
4272 ft²
- Oceanfront
- Fireplace/Heating
- Ocean View
- Balcony/Terrace
US $956/Night
7 Nights - US $6,694
Why Choose Rent By Owner for your Wilton 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 Wilton
When should you plan your Vacation Rentals stay?
Choosing the right time to vacation here ensures you experience the region's natural beauty and local charm at its best, making your stay more enjoyable and memorable.
Peak Season Highlights
Late Spring to Early Summer (May to June)
During this period, you can enjoy the area's pleasant weather and vibrant natural scenery, perfect for exploring or relaxing in your vacation rental. This is a popular time for travelers seeking an authentic experience of the region’s outdoor beauty.
Average Temperature Daytime: 70-80°F - Nighttime: 50-60°F
Fall (September to October)
The fall months bring colorful foliage and crisp air, making it an ideal time to stay in a comfortable vacation rental while enjoying the scenic surroundings. It’s a busy season for visitors looking to experience the region's seasonal charm.
Average Temperature Daytime: 65-75°F - Nighttime: 45-55°F
Off-Season Highlights
Winter (December to February)
Visit during winter for quieter accommodations and a peaceful atmosphere. While colder, this season offers a cozy retreat in well-equipped vacation rentals amidst the serene winter landscape.
Average Temperature Daytime: 30-40°F - Nighttime: 20-30°F
Early Spring (March to April)
In early spring, the area tends to be less crowded, providing a tranquil setting for your stay. Enjoy the gradual warming temperatures and budding nature from your vacation rental as the season transitions.
Average Temperature Daytime: 50-60°F - Nighttime: 35-45°F
Weekly Weather Forecast for Wilton
How to Book Your Wilton 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 Wilton
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 private outdoor patios or decks to relax amidst the natural surroundings.
- Make the most of spacious yards or gardens perfect for outdoor activities and gatherings.
- Take advantage of outdoor grilling facilities to experience alfresco dining in the region's pleasant climate.
- Benefit from access to picturesque walking trails or scenic pathways nearby for outdoor exploration.
- Relax by a private swimming pool or hot tub, ideal for unwinding after a day of exploring the area.
- Utilize outdoor fire pits or fireplaces for cozy evenings under the stars.
- Capitalize on well-maintained sports courts or game areas for active pursuits during your stay here.
Top Attractions Around Wilton
What attractions are nearby?
Nearby, you can explore a variety of outdoor activities and scenic spots that showcase the natural beauty of this destination, making your stay here both relaxing and engaging.
Family Activities
- Wilton Historical Society: Explore the region's rich history through interactive exhibits and engaging programs perfect for family outings.
- Copps Island Oyster Farm: Experience a hands-on tour of this local oyster farm where your family can learn about oyster farming and enjoy fresh tastings.
- Bradley Park: Spend a day outdoors in the area's scenic park, offering playgrounds, picnic areas, and walking trails for family fun and relaxation.
- Wilton Town Green: Attend seasonal festivals and community events that bring families together in the heart of this charming destination.
Adult Activities
- Wilton Historical Society Tour: Explore the region’s rich history by visiting this society’s exhibits and historic site tours, offering insight into the area's past.
- Farmers Market Experience: Visit the local farmers market for fresh produce and artisanal goods, perfect for a leisurely daytime activity in this destination.
- W Bridge Nature Preserve Walks: Enjoy scenic walking trails through this preserve, where you can observe native wildlife and relax amidst natural beauty.
- Golfing at Rolling Hills Country Club: Tee off at this renowned golf course, providing a challenging and scenic experience right here in the region.
Other Places to Stay in Wilton, CT
Gateway Shopping Center
Silvermine Golf Club
Wilton Historical Society
Weir Farm National Historic Site
Wilton Travel Tips
How Can You Make the Most of Your Stay?
- Explore Local Nature Spots: Take advantage of the region’s scenic parks and trails to enjoy outdoor activities and embrace the natural beauty surrounding your vacation rental.
- Plan Nearby Day Trips: Use the area as a base to visit nearby attractions and charming towns, ensuring you experience the full charm of this destination.
- Discover Culinary Gems: Savor local cuisine at nearby eateries or prepare homemade meals using fresh ingredients from local markets to enhance your stay.
- Engage with the Community: Participate in community events or visit local shops to gain a deeper understanding of the culture and character of this destination.
Transportation Options
- Metro-North Railroad: You can access reliable train services from the region, offering convenient transportation to New York City and other key destinations.
- Interstate 95: Traveling by car via this major highway provides easy connectivity for day trips or exploring nearby cities around the area.
- Local Bus Services: Local bus options offer affordable and straightforward transit within Wilton and its neighboring communities.
- Taxi and Rideshare Services: On-demand taxi and rideshare options present flexible transportation choices for getting around here seamlessly.
Local Customs Options
- Community Events and Festivals: Participating in local festivals is a cherished tradition here, offering you a chance to experience the area's vibrant culture and close-knit community spirit.
- Respect for Nature and Outdoor Etiquette: Visitors are encouraged to admire the natural beauty of this region responsibly by following outdoor etiquette and preserving its scenic landscapes.
- Historical Preservation Customs: The community values its historical heritage, so you’ll find locals often engaging in activities that celebrate and maintain the area's rich history.
- Dining and Social Norms: When dining out or attending gatherings, expect a warm, neighborly atmosphere where politeness and good manners are appreciated as part of the local customs.
Wilton Vacation Rental Frequently Asked Questions
1. What are the top vacation rentals in Wilton?
There are a lot of options in Wilton. If you plan on staying in the Wilton area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Wilton:
- Private French Country Estate-New Canaan CT-Pool-Film Set-August available
- Charming Cottage located on Historic Estate 1 Hour from NYC!
- Farmhouse 1899: Westport, CT - Minutes to Downtown, family and pet-friendly.
- Westport Gem - walk to shops, dining, town center, pet-friendly
- Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
- Spacious 5-bedroom house with waterfall view and walk to town
- Updated Farmhouse Retreat
- Gracious Country Home with Private Pool
- Charming Historic Connecticut Home W/Spacious Yard
- Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
2. How many vacation rentals have private pools in Wilton?
There are 26 vacation rentals with private pools near Wilton. Top-rated RBO homes that have access to a swimming pool include:
3. Which vacation homes in Wilton are best for families?
If you are looking for a family-friendly vacation home in Wilton, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Wilton:
4. How many Rentbyowner vacation rentals are available in Wilton?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 178 in the Wilton 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 Wilton.
5. What is the cancellation policy for vacation rentals in Wilton, Connecticut?
Cancellation policies vary depending on the property owner. You should review the specific listing details or contact the host directly to understand their cancellation terms before booking.
6. Are there any additional fees associated with my stay at a vacation rental here?
Additional fees such as cleaning fees, service charges, or security deposits are often specified in the listing. Be sure to read the property details carefully or reach out to the host for clarification.
7. How do I ensure my reservation is confirmed in this area?
Once you complete the booking process and receive confirmation from the host, your reservation is secured. Confirm all details and communicate with the host if you have special requests.
8. What amenities can I expect when staying at a vacation rental in this region?
Amenities differ among properties; common features include Wi-Fi, parking, kitchen facilities, and outdoor spaces. Check the listing description for a comprehensive list of included amenities.
9. How close are these vacation rentals to key attractions or transportation options in the area?
Property locations vary, so review the map and property description carefully for proximity to local attractions, public transportation, or major highways to plan your trip effectively.
Wilton Top Rated Vacation Rentals
House
10.0(21 Reviews)
3 Bedrooms
1 Bath
5 Guests
1800 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $470/Night
7 Nights - US $3,287
House
9.0(16 Reviews)
3 Bedrooms
2 Baths
8 Guests
1800 ft²
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $330/Night
7 Nights - US $2,312
Hotel
8.8(982 Reviews)
1 Bath
- Fireplace/Heating
- Pool
- Balcony/Terrace
- Kitchen
US $166/Night
7 Nights - US $1,159
House
8.8(8 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Fireplace/Heating
- Pool
- Pet Friendly
- Kitchen
US $393/Night
7 Nights - US $2,753
Hotel
8.3(131 Reviews)
14 Baths
329.07 ft²
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $253/Night
7 Nights - US $1,768
US $141/Night
7 Nights - US $984
Hotel
7.6(278 Reviews)
1 Bath
355.21 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Pet Friendly
US $264/Night
7 Nights - US $1,849
House
6.0(4 Reviews)
1 Bedroom
1 Bath
1 Guest
- Private Pool
- Fireplace/Heating
- Pool
- Balcony/Terrace
US $96/Night
7 Nights - US $671
