Weston Vacation Rentals from $152: Search Short-Term Rentals

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Our top choices for Weston vacation rentals

Classic Suite | Iron/ironing board, WiFi (free), bed sheets

1. DUNE Fairfield Beach

Fairfield Beach

slava

$235 nightly

Sep 28 - Sep 29

Total with taxes and fees

2. Spacious Studio with Pool Table

Westport

Eadweard

$226 nightly

Sep 22 - Sep 23

Total with taxes and fees

Standard Room, 1 King Bed, Main Building | Property entrance

3. Guesthouse at Norwalk Inn

Historic District

Ronbert

$327 nightly

Oct 21 - Oct 22

Total with taxes and fees

4. Luxury Designer 2 bedroom+office/3bed vacation home.

Brooklawn - St. Vincent

Anonymous traveler

$313 nightly

Sep 22 - Sep 23

Total with taxes and fees

1 bedroom, desk, iron/ironing board, WiFi (free)

5. Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

Downtown Bridgeport

Bailey

$205 nightly

Sep 23 - Sep 24

Total with taxes and fees

2 bedrooms, iron/ironing board, WiFi, bed sheets

6. Gilded Age Luxury Surrounded by Nature

Cranbury

$377 nightly

Sep 28 - Sep 29

Total with taxes and fees

Beach nearby, sun loungers, beach towels

7. Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

Fairfield

Kim G.

$541 nightly

Oct 21 - Oct 22

Total with taxes and fees

8. Elite room stay

Bridgeport

$289 nightly

Sep 22 - Sep 23

Total with taxes and fees

9. Centric property close to all the great things in the city

Brooklawn - St. Vincent

Alma B.

$226 nightly

Sep 22 - Sep 23

Total with taxes and fees

10. Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

Tunxis Hill

Parker M.

$288 nightly

Sep 22 - Sep 23

Total with taxes and fees

11. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

Historic District

Melissa H.

$649 nightly

Oct 21 - Oct 22

Total with taxes and fees

Coffee/tea maker, fridge, microwave, oven

12. Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

Fairfield

gail s.

$537 nightly

Oct 13 - Oct 14

Total with taxes and fees

Fridge, microwave, stovetop, cookware/dishes/utensils

13. Zen, Spacious & Comfy 2 bed, Lux beds

Brooklawn - St. Vincent

"Our host forgot we were coming, did not have check-in instructions or access, and did not respond to message or phone call. We had reserved this property to move my daughter across the country and into her dorm in college. Needless to say, an already stressful time was made more stressful as we had to find somewhere new to stay that evening that did not offer the same amenities we had planned on. Very disappointed and made for a rough start to our trip. I was pleased we received a full refund."

Sarah K.

$249 nightly

Sep 22 - Sep 23

Total with taxes and fees

14. Stamford Suites

Downtown Stamford

Alice

$169 nightly

Sep 27 - Sep 28

Total with taxes and fees

15. Modern 2 Bed in BlackRock

Black Rock Historic District

Joshua L.

$282 nightly

Sep 22 - Sep 23

Total with taxes and fees

16. Renovated 2BR Retreat / Modern Comforts Included

West End - West Side

Anonymous traveler

$288 nightly

Oct 6 - Oct 7

Total with taxes and fees

17. Nama-stay, sweet pink Saugatuck Shores beach cottage

Westport

Deb S.

$544 nightly

Sep 23 - Sep 24

Total with taxes and fees

18. 4 Mi to Beach & Dtwn! Charming Fairfield Home

Tunxis Hill

$652 nightly

Sep 22 - Sep 23

Total with taxes and fees

19. Business or Weekend escape

Stratford

Kimberly

$135 nightly

Oct 5 - Oct 6

Total with taxes and fees

20. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Waterside

Leslie S.

$286 nightly

Sep 30 - Oct 1

Total with taxes and fees

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Top Weston Hotel Reviews

Amsterdam Hotel

10/10 Excellent

"walking distance to downtown, nice staff, clean. great option for the price and location."

Comfort Inn & Suites Danbury-Bethel

8/10 Good

"The room was spacious. What I and my wife really liked was the engineered hard wood floor. Carpets are filthy and bacteria prone. The bath room was OK. The toilet and face sink were next to each other. The negative was that there was no place to hang the towels you are currently using. Another negative was that the shower bottom felt slippery even though it had a non slip bottom. The free breakfast was the usual fair. I did not like the coffee taste. The scrambled eggs were overcooked. The bacon was extra thin. The apple my wife had looked like it was picked last year. It was very dry and old. There was no ice water. The elevator was carpeted and filthy for the entire weekend. I would stay there again but I would ask for a room with a shower stall and no bathtub. The staff was excellent."

Find out more about Weston

Everything you need to know about Weston vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Weston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Weston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Weston vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Weston. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Weston in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $152 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Weston rentals

At Expedia, we put the best Weston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Weston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Weston vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Weston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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Frequently asked questions

Can I find a vacation rental in Weston?

Yes, there are vacation rentals close to well known attractions in Weston, or you can choose a secluded option if you want a relaxing place to stay.

What are some of the best vacation home rentals that Weston has to offer?

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed: This vacation home rental outside of Weston offers a fireplace, a patio, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many vacation rentals are there in Weston?

Choose from 13 Expedia vacation rentals in Weston for a memorable vacation.

What’s there to see and do in Weston?

While exploring the area, visit family-friendly sights like Stepping Stones Museum for Children, or get outside and enjoy nature at Lucius Pond Ordway / Devil's Den Preserve. Trout Brook Valley State Park Reserve and Wilton Historical Society are a couple of places you'll find in the larger area.

What’s a vacation rental in Weston like?

Vacation rentals are private properties you can reserve for a short or long stay in Weston. Vacation rentals feature extras like kitchens and laundry facilities so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from shared hotel elevators and busy front desks while still allowing you to travel. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive choice for families.

Weston Vacation Rentals

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Check prices for these dates

Our top choices for Weston vacation rentals

1. DUNE Fairfield Beach

2. Spacious Studio with Pool Table

3. Guesthouse at Norwalk Inn

4. Luxury Designer 2 bedroom+office/3bed vacation home.

5. Lovely Bohemian Loft Downtwn, Amphitheater,Seaside Park,Metro North,2-10min walk

6. Gilded Age Luxury Surrounded by Nature

7. Cozy Cottage with Fire Pit, near Beach, 1 mile to NYC train

8. Elite room stay

9. Centric property close to all the great things in the city

10. Sunny & Spacious 2BD, 1BA WFH Apt-Huge Yard & Patio

11. Family Cottage with 4 King Beds and Fire Pit, Norwalk/Westport Border

12. Renovated Cape Near beach, with Fire Pit and BBQ, 1 mile to NYC train

13. Zen, Spacious & Comfy 2 bed, Lux beds

14. Stamford Suites

15. Modern 2 Bed in BlackRock

16. Renovated 2BR Retreat / Modern Comforts Included

17. Nama-stay, sweet pink Saugatuck Shores beach cottage

18. 4 Mi to Beach & Dtwn! Charming Fairfield Home

19. Business or Weekend escape

20. Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Find vacation rentals that suit your style

Top Weston Hotel Reviews

Amsterdam Hotel

Find out more about Weston

Explore a world of travel with Expedia

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