Vacation rentals in Weston

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Top-rated vacation rentals in Weston

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Guest favorite

Guest suite in Fairfield

4.92 out of 5 average rating, 109 reviews

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; for stays of 1 week or less: exclusive use of main kitchen; private entrance to space. Includes continental breakfast, 2 large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.

Dec 21 – 28

$102 per night

Guest favorite

Guesthouse in Wilton

4.96 out of 5 average rating, 96 reviews

The Cozy Little Cottage

Charming guest cottage on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 minutes to Westport center. The cottage is separate from the main house, connected by a breezeway, above the garage. It is a quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and dishwasher drawer. The bedroom has a queen bed and the living room has a futon couch which folds down. We also have a twin air mattress. It is perfect for one or two people.

Jul 17 – 24

$134 per night

Guest favorite

Guest suite in Fairfield

4.93 out of 5 average rating, 110 reviews

Adorable private apt w/ W/D in lovely neighborhood

Enjoy a lovely experience at this centrally-located studio in-law apartment. It boasts a newly renovated kitchen and bath, king bed with brand new mattress, pull out full size sofa, ample closet space and more. The eat-in kitchen has all you need to feel right at home. The apartment is located adjacent to a nice residential house, but is fully private with your own front and back entrances. There are also no stairs, making it easily accessible. It’s located in a wonderful neighbor in Fairfield.

May 9 – 16

$113 per night

Guest favorite

Guest suite in Wilton

4.9 out of 5 average rating, 103 reviews

Serene Pond Views charming private patio…

Country Charm Awaits. 45 miles north of George Washington Bridge. Our 2 room efficacy apartment w. microwave, mini fridge & private entrance + parking space. Great WiFi, Apple TV. Enjoy views overlooking Henderson Pond. 1/4 walk to Query State Park, 36 acres w. trails. Our apartment is 4 miles from town of Ridgefield, 3 miles from Wilton town center, 6 miles from New Caanan & 8 miles from Westport Town Center. We have a couple of small puppies who will welcome you too. So we don’t allow pets…

Oct 24 – 31

$122 per night

Guest favorite

Apartment in Westport

4.93 out of 5 average rating, 114 reviews

Spacious Westport Apt surrounded by nature

Spacious mother-in-law apartment w/ private entrance on the 1st floor of our beautiful home. Windows in every room give view to the creek in the backyard and birds welcoming our guests. Two bedrooms with a queen size bed. Walk-in shower. Plenty of space up to four people. Very family friendly - little humans and furry friends welcome! Centrally located 8-10 min drive to downtown Westport, Fairfield, or Southport. Beach, golf course, playgrounds, and wonderful bakeries and restaurants nearby!

Jan 26 – Feb 2

$155 per night

Guest favorite

Cottage in Weston

4.97 out of 5 average rating, 31 reviews

The River Loft

Escape to The River Loft, a secluded private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Jan 22 – 29

$315 per night

Guest favorite

Guesthouse in Norwalk

4.99 out of 5 average rating, 207 reviews

Adorable one-bedroom guesthouse with parking

Private, peaceful, cozy renovated cottage next to my house in a quiet residential neighborhood. Originally used as a painting and design studio, ideal for short stays and as a workspace. Luxury queen bed in upstairs loft; downstairs with refrigerator/freezer, Keurig with coffee and tea; microwave; Wifi, heat, air conditioning. There is NO RUNNING WATER in the cottage, but a lovely PRIVATE FULL BATH is just steps away in the main house AVAILABLE 24/7 exclusively for you during your stay.

Mar 4 – 11

$113 per night

Guest favorite

Cottage in Easton

4.98 out of 5 average rating, 190 reviews

Cozy Modern Cottage with Fireplace

Clean, modern + large, our guest house has all the amenities and comforts of home. Cottage is dressed in whites and neutrals with natural light and plants throughout for a sacred, restful feel. Full kitchen, king bed, gas fireplace, laundry and spacious grounds with meditation hill, fire pit, stone fences, and nearby hiking trails. Pool and hot tub May-Sept. Come relax in New England's stunning natural beauty. Read our photo captions for more details. We look forward to meeting you!

May 3 – 10

$127 per night

Guest favorite

Apartment in Redding

4.94 out of 5 average rating, 459 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

Now is the time to book your spring getaway to the Huckleberry Quarters, a totally renovated (2015) studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A Perfect weekend getaway or writing/artist space. Easy access to Merritt Parkway, trains, local eateries, parks.

Aug 13 – 20

$125 per night

Guest favorite

Apartment in Brookfield

4.94 out of 5 average rating, 184 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.

Feb 21 – 28

$103 per night

Guest favorite

Guest suite in Wilton

5.0 out of 5 average rating, 33 reviews

Guest suite with private enter

Private room with private enter and bathroom attached dedicated work space and privat parking. On a 1.5 acres property. With fast internet. Located 5 minutes of walking distance from ASML office park, 5 minutes drive from Norwalk corporate park, 9 minutes drive from Wilton Downtown and 15 min drive from Norwalk train station. Close to a lot of restaurants, coffee shops, stores and parks. The owners live in other part of the house. Family owns cats.

Jul 7 – 14

$81 per night

Guest favorite

Place to stay in Westport

4.96 out of 5 average rating, 278 reviews

Sunny Westport 2 BR Retreat above Historic Mill

This eclectic, sunny, spot, sits above a renovated historic cider mill from the 1850s. It has been designed and furnished by our own team of artisans. With panoramic views and breathtaking surroundings, including endless flora and fauna, and a contingent of mallards, egrets, and swans, this hideaway is the perfect "Get Away."

Jan 17 – 24

$178 per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Weston vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Stay near Weston's top sights

Orem's Diner4 locals recommend

Wire Mill Saloon & Barbeque7 locals recommend

Devil's Den Preserve32 locals recommend

Peter's Weston Market6 locals recommend

Lunch Box6 locals recommend

Milestone6 locals recommend

Other great vacation rentals in Weston

Guest favorite

Guest suite in Weston

5.0 out of 5 average rating, 28 reviews

Renovated 1Bed Suite, Full Kitchen, 5 min>Westport

Feb 7 – 14

$220 per night

Guest favorite

Guesthouse in Weston

5.0 out of 5 average rating, 50 reviews

Adorable 1-Bedroom Cottage w/ Mezzanine Weston, CT

Oct 6 – 13

$176 per night

Guest favorite

Guesthouse in Weston

4.96 out of 5 average rating, 24 reviews

Nature Lovers Guesthouse

Aug 17 – 24

$259 per night

Superhost

Home in Weston

4.8 out of 5 average rating, 10 reviews

Magical Weston Retreat

Dec 13 – 20

$217 per night

Guest favorite

Guesthouse in Wilton

5.0 out of 5 average rating, 21 reviews

The Ciderhouse Cottage - private escape in Wilton

Sep 23 – 30

$283 per night

Guest favorite

Apartment in Westport

4.92 out of 5 average rating, 13 reviews

Westport CT, Hide-away!

May 6 – 13

$157 per night

Guest favorite

Apartment in Fairfield

4.95 out of 5 average rating, 62 reviews

Sunny Fairfield Studio Apartment

Aug 4 – 11

$118 per night

Guest favorite

Cottage in Bethel

5.0 out of 5 average rating, 57 reviews

The Sweet Retreat near Bethel & Newtown, King Bed

Apr 17 – 22

$129 per night

Show all

Quick stats about vacation rentals in Weston

Total rentals
50 properties
Rentals with a pool
10 properties have a pool
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
890 reviews
Nightly prices starting at
$40 before taxes and fees

Frequently Asked Questions

Are there pet-friendly vacation rentals in Weston?
Four-legged friends are welcome in Weston. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Weston?
Yes! Work meets play with ease at over 40 vacation rentals in Weston featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Weston have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Weston. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in house rentals in Weston?
Experience the best of Weston with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do house rentals in Weston have wifi?
Absolutely! We offer over 30 house rentals with wifi in Weston. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Weston?
Enhance your stay in our House Rentals with the most popular amenities: over 30 homes with air conditioning, over 30 homes with free parking, over 30 homes with wifi, over 30 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do house rentals in Weston have free parking?
Absolutely! We offer over 30 house rentals with free parking in Weston. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly vacation rentals in Weston?
Weston has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Weston have a kitchen?
Absolutely! We offer over 30 house rentals with a kitchen in Weston. Enjoy a tailored experience with all the comforts you desire.
Are there Weston vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Weston, available on Airbnb. Make a splash and soak up the sun in style!

Vacation rentals in Weston

Top-rated vacation rentals in Weston

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Weston vacation rentals

Stay near Weston's top sights

Other great vacation rentals in Weston

Guest suite in Weston

Guesthouse in Weston

Guesthouse in Weston

Home in Weston

Guesthouse in Wilton

Apartment in Westport

Apartment in Fairfield

Cottage in Bethel

Quick stats about vacation rentals in Weston

Total rentals

Rentals with a pool

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there pet-friendly vacation rentals in Weston?

Are there vacation rentals with a dedicated workspace in Weston?

Do house rentals in Weston have air conditioning?

How much does it cost to stay in house rentals in Weston?

Do house rentals in Weston have wifi?

What are the most popular amenities for House Rentals in Weston?

Do house rentals in Weston have free parking?

Are there family-friendly vacation rentals in Weston?

Do house rentals in Weston have a kitchen?

Are there Weston vacation rentals on Airbnb with pools?

Destinations to explore