Short-Term Rentals in Weston, CT: Compare 10+ Sites & Save

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80 Best Short-Term Rentals in Weston (Starting from $95)

Historic Connecticut Home with Grill and Spacious Yard
Historic Connecticut Home with Grill and Spacious Yard
House
Weston, CT, USA
1.1k from Weston center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms7 Guests
New to Booking
$412
Average price / night
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Charming Historic Connecticut Home W/Spacious Yard
Charming Historic Connecticut Home W/Spacious Yard
House
Weston, CT, 06883, United States
1.1k from Weston center

AC, Barbecue, Dryer, Heater, Internet, Kitchen, Microwave, No Smoking, Patio

4 Bedrooms7 Guests
10.0

Exceptional

2 reviews

$567
Average price / night
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Cozy Retreat Near Westport
Cozy Retreat Near Westport
House
Fairfield, CT, USA
4.3k from Weston center

View, Security/Safety, Guest Services, Air Conditioner, Parking, Child Friendly

1 Bedroom2 Guests
New to Booking
$180
Average price / night
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A private room for any traveler
A private room for any traveler
House
Weston, CT, 06883, United States
1.6k from Weston center

AC, Free Parking, Heater, Internet, No Smoking, Outdoor Space, Patio, Pool

1 Bedroom1 Guest
6.0

Review score

4 reviews

$95
Average price / night
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Relaxing 2 Bedroom 2 Bath Apt in Beautiful Nature
Relaxing 2 Bedroom 2 Bath Apt in Beautiful Nature
Apartment
Weston, Connecticut, USA
4.8k from Weston center

Air Conditioner, Parking, Balcony/Terrace, Pet Friendly, Internet, Child Friendly

2 Bedrooms3 Guests
New to Booking
$179
Average price / night
Check Availability
Cozy, fully renovated 2BR home with a barn in peaceful Weston, CT for relaxation
Cozy, fully renovated 2BR home with a barn in peaceful Weston, CT for relaxation
House
Weston, CT, 06883, United States
1.8k from Weston center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$359
Average price / night
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Light filled zen 3BR Penthouse - 7 min to Westport
Light filled zen 3BR Penthouse - 7 min to Westport
Apartment
Weston, CT, USA
4.8k from Weston center

Apartments, Accommodations, Parking, Lodgings, Places to stay

3 Bedrooms5 Guests
New to Booking
$512
Average price / night
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Luxury 3-Acre Estate: Private Pool, Basketball Court & Designer Interiors
Luxury 3-Acre Estate: Private Pool, Basketball Court & Designer Interiors
House
Weston, CT, 06883, United States
2.1k from Weston center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
New to Booking
$1150
Average price / night
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Main Street Stay Westport
Main Street Stay Westport
House
Westport, CT, USA
5.8k from Weston center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom8 Guests
New to Booking
$633
Average price / night
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Modern 4 bed 4.5 bath w hot tub & heated pool close to beach
Modern 4 bed 4.5 bath w hot tub & heated pool close to beach
House
Weston, CT, 06883, United States
2.5k from Weston center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms8 Guests
9.8

Exceptional

6 reviews

$1292
Average price / night
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Luke's Landing
Luke's Landing
House
Westport, CT, USA
6.2k from Weston center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$291
Average price / night
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50%OFF Riverfront WestonHome 1.6 Acers-NYC 1 hour Near estaurants I-95& Parkway
50%OFF Riverfront WestonHome 1.6 Acers-NYC 1 hour Near estaurants I-95& Parkway
House
Weston, CT, 06883, United States
2.9k from Weston center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms6 Guests
7.4

Good

14 reviews

$202
Average price / night
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Modern Westport Studio with Pool Table & Lounge
Modern Westport Studio with Pool Table & Lounge
Apartment
Westport, CT, USA
7.0k from Weston center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay

1 Bedroom4 Guests
8.0

Good

4 reviews

$280
Average price / night
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Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport.
Newly renovated 6BR, Pool, Spa, ScreenPorch, 2 private acres, Heart of Westport.
House
Westport, CT, 06880, United States
3.0k from Weston center

AC, Arcade, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

6 Bedrooms12 Guests
New to Booking
$1437
Average price / night
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Norwalk Retreat
Norwalk Retreat
House
CT, USA
9.8k from Weston center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$509
Average price / night
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Newly renovated summer home in Westport CT private pool & spa, near beach & town
Newly renovated summer home in Westport CT private pool & spa, near beach & town
House
Westport, CT, 06880, United States
3.3k from Weston center

AC, Arcade, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub

6 Bedrooms12 Guests
New to Booking
$1470
Average price / night
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Sunny Westport Studio Apt. Above Historic Mill
Sunny Westport Studio Apt. Above Historic Mill
Apartment
Westport, CT, USA
9.8k from Weston center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Beach, Places to stay, Family

1 Bedroom3 Guests
9.5

Superb

4 reviews

$390
Average price / night
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Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Escape to 'River Cottage. Ready for hiking, fishing, or a peaceful break?
Cottage
Weston, CT, 06883, United States
3.6k from Weston center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

2 Bedrooms4 Guests
10.0

Exceptional

13 reviews

$431
Average price / night
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Sunny Westport 2 BR Retreat above Historic Mill
Sunny Westport 2 BR Retreat above Historic Mill
Apartment
Westport, CT, USA
9.8k from Weston center

Apartments, Cheap, Accommodations, Parking, Pet-friendly, Lodgings, Places to stay, Family

2 Bedrooms5 Guests
9.5

Superb

2 reviews

$393
Average price / night
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Charming 3-bedroom Ranch in Weston Near Westport & Fairfield
Charming 3-bedroom Ranch in Weston Near Westport & Fairfield
House
Weston, CT, 06883, United States
4.0k from Weston center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$519
Average price / night
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Interior Designer's Enchanting Home with Private Beach 1.5hrs from Brooklyn
Interior Designer's Enchanting Home with Private Beach 1.5hrs from Brooklyn
House
Weston, CT, 06883, United States
4.2k from Weston center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$1623
Average price / night
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Charming 4-bedroom house with AC and WiFi in fabulous Westport
Charming 4-bedroom house with AC and WiFi in fabulous Westport
House
Westport, CT, 06880, United States
4.5k from Weston center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

4 Bedrooms6 Guests
New to Booking
$1002
Average price / night
Check Availability
Westport Family Friendly Oasis
Westport Family Friendly Oasis
House
Westport, CT, 06880, United States
4.6k from Weston center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking

6 Bedrooms12 Guests
New to Booking
$1562
Average price / night
Check Availability
Relaxing apartment in weston woods
Relaxing apartment in weston woods
Cottage
Weston, CT, 06883, United States
4.8k from Weston center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

2 Bedrooms3 Guests
New to Booking
$171
Average price / night
Check Availability
Designer Treehouse with Spa Bath
Designer Treehouse with Spa Bath
Apartment
Wilton, CT, 06897, United States
4.8k from Weston center

AC, Crib, Dryer, Elevator, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$691
Average price / night
Check Availability
Spacious 6-bedroom 5 bathroom Dream House, with salt water pool & stone hot tub.
Spacious 6-bedroom 5 bathroom Dream House, with salt water pool & stone hot tub.
House
Westport, CT, 06880, United States
4.9k from Weston center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

5 Bedrooms13 Guests
New to Booking
$2109
Average price / night
Check Availability
Spacious 5-bedroom house with waterfall view and walk to town
Spacious 5-bedroom house with waterfall view and walk to town
House
Westport, CT, 06880, United States
4.9k from Weston center

AC, Dryer, Heater, Laundry, No Smoking, Washer

5 Bedrooms10 Guests
New to Booking
$862
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Weston.

Stay Near Weston's Top Attractions

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Weston Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 80 verified short-term rentals in Weston, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Weston vary depending on location, property size, and travel dates. Rates typically start from around $95 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Weston include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Weston, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Weston often include amenities such as Fireplace/Heating, Bedding/Linens, and Laundry, providing a comfortable and convenient stay.

Short-term rentals in Weston are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.