Wilton Holiday Rentals
House
10.0Exceptional
(17 Reviews)
2 Bedrooms
2 Baths
4 Guests
Parking
Balcony/Terrace
Kitchen
Air Conditioner
US $528/Night
7 Nights - US $3,695
House
9.0Exceptional
(1 Review)
3 Bedrooms
4 Baths
8 Guests
3282.99 ft²
Private Beach
Oceanfront
Breakfast
EV Charge Station
US $515/Night
7 Nights - US $3,605
Bed & Breakfast
- Danbury
- ·
- Ridgefield
- 1.99 mi to center
9.8Exceptional
(54 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $430/Night
7 Nights - US $3,009
Cottage
- Connecticut
- ·
- Weston
- 2.26 mi to center
10.0Exceptional
(15 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Kitchen
- Air Conditioner
Internet
US $501/Night
7 Nights - US $3,510
Apartment
6.3Good
(3 Reviews)
2 Bedrooms
2 Baths
4 Guests
247.57 ft²
- Parking
- Air Conditioner
- Internet
Pet Friendly
US $206/Night
7 Nights - US $1,439
Cottage
- Stamford
- ·
- New Canaan
- 1.82 mi to center
10.0Exceptional
(6 Reviews)
2 Bedrooms
2 Baths
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $721/Night
7 Nights - US $5,045
House
- Connecticut
- ·
- Weston
- 1.11 mi to center
10.0Exceptional
(2 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Air Conditioner
- Internet
Child Friendly
Laundry
US $444/Night
7 Nights - US $3,105
Apartment
9.4Exceptional
(3 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $276/Night
7 Nights - US $1,934
House
- Connecticut
- ·
- Weston
- 1.01 mi to center
6.0Good
(4 Reviews)
1 Bedroom
1 Bath
1 Guest
Private Pool- Parking
Pool- Balcony/Terrace
US $96/Night
7 Nights - US $671
Luxury Holiday Rentals in Wilton
Over 170+ Luxury Holiday Rentals in or Near Wilton
House
6 Bedrooms
5 Baths
9 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $2,520/Night
7 Nights - US $17,637
House
10.0Exceptional
(1 Review)
8 Bedrooms
8 Baths
15 Guests
- Private Pool
Hot Tub- Parking
- Pool
US $2,393/Night
7 Nights - US $16,751
New
House
6 Bedrooms
5 Baths
12 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $2,291/Night
7 Nights - US $16,037
House
6 Bedrooms
6 Baths
14 Guests
- Hot Tub
- Pool
- Balcony/Terrace
- Kitchen
US $2,219/Night
7 Nights - US $15,533
New
House
5 Bedrooms
4 Baths
13 Guests
4750 ft²
- Hot Tub
- Parking
- Pool
- Kitchen
US $2,118/Night
7 Nights - US $14,826
House
- Stamford
- ·
- New Canaan
- 1.62 mi to center
10.0Exceptional
(5 Reviews)
5 Bedrooms
4 Baths
15 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,852/Night
7 Nights - US $12,963
Villa
- Stamford
- ·
- New Canaan
- 2.43 mi to center
4 Bedrooms
2 Baths
8 Guests
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $1,619/Night
7 Nights - US $11,330
House
- Connecticut
- ·
- Weston
- 1.54 mi to center
9.8Exceptional
(8 Reviews)
5 Bedrooms
4 Baths
8 Guests
4300 ft²
- Private Pool
- Oceanfront
- Hot Tub
- Parking
US $1,394/Night
7 Nights - US $9,758
House
10.0Exceptional
(7 Reviews)
5 Bedrooms
4 Baths
8 Guests
4840 ft²
- Oceanfront
- Hot Tub
- Parking
Ocean View
US $1,290/Night
7 Nights - US $9,027
Top-Rated Holiday Rentals with a Pool in Wilton
Over 48+ The Best Private Villas and Holiday Rentals in Wilton with a Pool
House
10.0Exceptional
(26 Reviews)
3 Bedrooms
1 Bath
5 Guests
1800 ft²
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $603/Night
7 Nights - US $4,223
House
10.0Exceptional
(2 Reviews)
5 Bedrooms
4 Baths
9 Guests
4700 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $953/Night
7 Nights - US $6,671
House
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
10 Guests
2900 ft²
- Hot Tub
- Parking
- Pool
- Ocean View
US $858/Night
7 Nights - US $6,003
House
9.0Exceptional
(4 Reviews)
3 Bedrooms
3 Baths
5 Guests
2636 ft²
- Private Pool
- Oceanfront
- Parking
- Pool
US $819/Night
7 Nights - US $5,734
Hotel
8.8Fabulous
(996 Reviews)
1 Bath
- Parking
- Pool
- Balcony/Terrace
- Kitchen
US $166/Night
7 Nights - US $1,159
House
8.8Fabulous
(8 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $489/Night
7 Nights - US $3,425
Hotel
8.4Excellent
(134 Reviews)
14 Baths
329.07 ft²
- Private Pool
- Breakfast
- Parking
- Pool
US $418/Night
7 Nights - US $2,923
Hotel
8.2Excellent
(1003 Reviews)
1 Bath
- Parking
- Pool
- Kitchen
- Air Conditioner
US $159/Night
7 Nights - US $1,116
Hotel
7.6Very Good
(278 Reviews)
1 Bath
355.21 ft²
- Private Pool
- Pool
- Balcony/Terrace
- Air Conditioner
US $264/Night
7 Nights - US $1,849
Pet-Friendly Holiday Rentals in Wilton
Over 73+ Pet-Friendly Holiday Rentals in or Near Wilton
Cottage
- Connecticut
- ·
- Weston
- 3.01 mi to center
2 Bedrooms
2 Baths
3 Guests
- Oceanfront
- Ocean View
View- Air Conditioner
US $165/Night
7 Nights - US $1,153
House
- Connecticut
- ·
- Weston
- 0.66 mi to center
3 Bedrooms
3 Baths
7 Guests
2798.62 ft²
- Parking
- Balcony/Terrace
- Internet
- Pet Friendly
US $412/Night
7 Nights - US $2,884
Apartment
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Pet Friendly
- Child Friendly
US $166/Night
7 Nights - US $1,159
Cottage
9.6Exceptional
(50 Reviews)
2 Bedrooms
1 Bath
3 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $334/Night
7 Nights - US $2,339
House
4 Bedrooms
3 Baths
8 Guests
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $853/Night
7 Nights - US $5,970
House
10.0Exceptional
(20 Reviews)
3 Bedrooms
2 Baths
9 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $937/Night
7 Nights - US $6,561
House
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
- Oceanfront
- Hot Tub
- Parking
- Ocean View
US $984/Night
7 Nights - US $6,885
House
- Connecticut
- ·
- Weston
- 2.51 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
3 Baths
6 Guests
- Parking
- Kitchen
- Air Conditioner
- Internet
US $807/Night
7 Nights - US $5,646
House
10.0Exceptional
(1 Review)
3 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,127/Night
7 Nights - US $7,886
Large Holiday Rentals and Private Villas in Wilton
Over 35+ Large Holiday Rentals and Private Villas in or Near Wilton
House
3 Bedrooms
2 Baths
10 Guests
- Private Pool
- Oceanfront
- Pool
- Ocean View
US $1,186/Night
7 Nights - US $8,300
New
Villa
1 Bedroom
1 Bath
5 Guests
990.28 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $230/Night
7 Nights - US $1,607
House
6 Bedrooms
5 Baths
10 Guests
4272 ft²
- Oceanfront
- Parking
- Ocean View
- Balcony/Terrace
US $1,156/Night
7 Nights - US $8,094
House
9.6Exceptional
(51 Reviews)
6 Bedrooms
6 Baths
15 Guests
- Hot Tub
- Parking
Spa- Ocean View
US $1,112/Night
7 Nights - US $7,787
New
House
- Stamford
- ·
- New Canaan
- 1.40 mi to center
5 Bedrooms
4 Baths
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $964/Night
7 Nights - US $6,745
House
10.0Exceptional
(9 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Balcony/Terrace
- Kitchen
- Air Conditioner
- Child Friendly
US $798/Night
7 Nights - US $5,589
House
10.0Exceptional
(9 Reviews)
5 Bedrooms
3 Baths
10 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $863/Night
7 Nights - US $6,038
House
- Stamford
- ·
- New Canaan
- 0.46 mi to center
10.0Exceptional
(5 Reviews)
5 Bedrooms
6 Baths
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $2,005/Night
7 Nights - US $14,032
Villa
10.0Exceptional
(3 Reviews)
7 Bedrooms
4 Baths
14 Guests
12000 ft²
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $882/Night
7 Nights - US $6,171
Wheelchair Accessible Holiday Homes in Wilton
Over 10+ Wheelchair Accessible Holiday Homes in or Near Wilton
Condo
1 Bedroom
1 Bath
4 Guests
600 ft²
- Parking
- Pool
- Ocean View
- Balcony/Terrace
US $199/Night
7 Nights - US $1,392
Hotel
8.4Excellent
(47 Reviews)
1 Bath
339.06 ft²
- Oceanfront
- Ocean View
- Balcony/Terrace
- View
US $512/Night
7 Nights - US $3,584
Hotel
9.2Exceptional
(1005 Reviews)
1 Bath
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $183/Night
7 Nights - US $1,280
House
10.0Exceptional
(2 Reviews)
4 Bedrooms
6 Baths
10 Guests
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,280/Night
7 Nights - US $8,960
Hotel
7.9Very Good
(445 Reviews)
12 Baths
290.63 ft²
- Parking
- Balcony/Terrace
- View
- Air Conditioner
US $181/Night
7 Nights - US $1,266
House
10.0Exceptional
(1 Review)
6 Bedrooms
7 Baths
11 Guests
6400 ft²
- Private Pool
- Parking
- Pool
- Ocean View
US $2,000/Night
7 Nights - US $14,000
Hotel
6.9Good
(343 Reviews)
5 Baths
301.39 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $145/Night
7 Nights - US $1,017
House
4 Bedrooms
5 Baths
8 Guests
- Private Pool
- Pool
- Balcony/Terrace
- Kitchen
US $1,000/Night
7 Nights - US $7,000
House
4 Bedrooms
4 Baths
8 Guests
4500 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $757/Night
7 Nights - US $5,299
Wilton Private Villas and Holiday Homes Under $200
Over 22+ Wilton Private Villas and Holiday Homes Under $200
Apartment
- Connecticut
- ·
- Weston
- 3.26 mi to center
1 Bedroom
1 Bath
2 Guests
500 ft²
- Oceanfront
- Parking
- Ocean View
- View
US $155/Night
7 Nights - US $1,085
Apartment
- Connecticut
- ·
- Weston
- 2.95 mi to center
2 Bedrooms
2 Baths
3 Guests
1399.31 ft²
- Parking
- Balcony/Terrace
- Air Conditioner
- Internet
US $179/Night
7 Nights - US $1,253
Hotel
6.4Good
(1004 Reviews)
1 Bath
- Parking
- Kitchen
- Air Conditioner
- Internet
US $117/Night
7 Nights - US $821
Cottage
- Connecticut
- ·
- Weston
- 3.28 mi to center
8.0Excellent
(1 Review)
1 Bedroom
1 Bath
2 Guests
500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $168/Night
7 Nights - US $1,176
Hotel
6.6Good
(263 Reviews)
6 Baths
301.39 ft²
- Parking
- Air Conditioner
- Internet
- Pet Friendly
US $116/Night
7 Nights - US $813
House
- Connecticut
- ·
- Weston
- 1.80 mi to center
7.4Very Good
(14 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $160/Night
7 Nights - US $1,119
Apartment
4.8Average
(3 Reviews)
1 Bedroom
1 Bath
2 Guests
- Breakfast
- Parking
- Balcony/Terrace
- Kitchen
US $165/Night
7 Nights - US $1,154
Cottage
- Connecticut
- ·
- Weston
- 2.95 mi to center
2 Bedrooms
2 Baths
3 Guests
1400 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $163/Night
7 Nights - US $1,139
Apartment
1 Bedroom
1 Bath
2 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $129/Night
7 Nights - US $900
Instantly Bookable Holiday Homes in Wilton
Over 56+ Instantly Bookable Holiday Homes in or Near Wilton
Apartment
- Stamford
- ·
- New Canaan
- 0.72 mi to center
2 Bedrooms
1 Bath
6 Guests
- Air Conditioner
- Internet
- Laundry
TV
US $673/Night
7 Nights - US $4,708
Apartment
1 Bedroom
1 Bath
2 Guests
- Air Conditioner
- Internet
- Child Friendly
- Laundry
US $130/Night
7 Nights - US $913
Hotel
- Danbury
- ·
- Ridgefield
- 1.99 mi to center
10.0Exceptional
(2 Reviews)
1 Bath
- Breakfast
- Parking
- Air Conditioner
- Child Friendly
US $474/Night
7 Nights - US $3,316
Hotel
- Danbury
- ·
- Ridgefield
- 1.99 mi to center
10.0Exceptional
(1 Review)
1 Bath
- Breakfast
- Parking
- Air Conditioner
- Child Friendly
US $486/Night
7 Nights - US $3,404
Hotel
- Danbury
- ·
- Ridgefield
- 1.99 mi to center
10.0Exceptional
(1 Review)
1 Bath
- Breakfast
- Parking
- Air Conditioner
- Child Friendly
US $448/Night
7 Nights - US $3,134
Hotel
- Danbury
- ·
- Ridgefield
- 1.99 mi to center
9.6Exceptional
(4 Reviews)
1 Bath
- Breakfast
- Parking
- Air Conditioner
- Child Friendly
US $422/Night
7 Nights - US $2,952
US $889/Night
7 Nights - US $6,221
US $812/Night
7 Nights - US $5,681
US $425/Night
7 Nights - US $2,973
Book a Last Minute Place to Stay in Wilton
About Casai's Private Villas and Holiday Rentals in Wilton
Discover more than 179 vacation rentals available in Wilton. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Wilton.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Wilton, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Wilton. On average, places to stay near Wilton offer 1069.05 ft², with nightly prices averaging US $704.
With Casai, finding and comparing holiday rentals in Wilton is easy and secure, often at a 30-40% discount compared to hotel prices. Simply search for your destination and secure your reservation today.
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Top Accommodation Types in Wilton
| Type | Count |
|---|---|
| Vacation Homes | 100 |
| Holiday Apartments | 28 |
| Cottages | 18 |
| Villas | 4 |
Use these Quick Filters to Find a Holiday Rental in Wilton
★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Wilton.
Weather in Wilton, CT
View the weather forecast for Wilton before booking your Wilton Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Wilton, CT
Casai offers a large selection of top attractions around Wilton . Research things to do on your vacation before you visit Wilton.
Other Places to Stay in Wilton, CT
Frequently Asked Questions About Wilton?
What are the top holiday rentals in Wilton?
With numerous options available in Wilton, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Wilton:
- 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?
- Your Summer Retreat, Modern and Spacious 5-bed house in marvelous Westport, CT!
- Charming 2 Bedroom Cottage in Peaceful New Canaan - Pet Friendly!
- Gracious Country Home with Private Pool
- Modern Farmhouse
- Summer getaway with Pool and Fully stocked Chef's Kitchen
- Charming 3-bedroom Ranch in Weston Near Westport & Fairfield
How many holiday rentals have private pools in Wilton?
Discover a selection of holiday rentals with private pools near Wilton with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.
- European style country chic with pool & privacy!
- 3-bedroom house in pleasant Norwalk with Pool, outdoor BBQ, and so much more
- Westport Summer Estate
- Beautiful Summer Escape
Which holiday homes in Wilton are best for families?
If you're searching for a family-friendly holiday home in Wilton, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Wilton:
- The West Lane Inn - Queen Studio Suite with Kitchenette
- South Salem Vacation Rental w/Furnished Deck!
- Days Inn by Wyndham Ridgefield
How many Casai.com holiday rentals are available in Wilton?
As of 2026, Casai boasts over 179 properties listed in the Wilton area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Wilton.
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