House vacation rentals in Bridgeport

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Popular amenities for Bridgeport house rentals

House rentals with a hot tub

Top guest favorite
Home in North Fork
4.97 out of 5 average rating, 205 reviews

Private Oasis W/Stunning Vinyard and Pool Views

RebeccaRating, 5 stars3 weeks ago
We loved staying at this home - it was the perfect place for our group of ten. The outdoor space was definitely the highlight, with the pool & spa being our favorite part of the trip. The only thing to note is that we weren’t supplied quite enough toilet paper or paper towels, though I did not reach out for more - It was the last evening when we ran out and we were leaving early the next morning. The trash requirements were a surprise after booking, but going to the transfer station was easy enough, and it is listed on the house rules. Overall, an excellent stay and would absolutely return!
Top guest favorite
Home in Wading River
4.96 out of 5 average rating, 503 reviews

Your Zen Retreat

LisaRating, 5 stars3 weeks ago
This was the most beautiful house in a private area in Wading River. It offers peace and tranquility and lives up to its name of Zen Retreat. It was exactly what we were seeking. Conveniently located near parks, farms and wineries I would definitely go back to Brian’s AirBNB. He was an excellent host and very responsive to our needs. Thank you Brian.
Superhost
Home in Port Jefferson
4.81 out of 5 average rating, 329 reviews

The Hilltop Harborview

DarrellRating, 5 stars6 days ago
Very quiet and peaceful.
Top guest favorite
Home in Pawling
5 out of 5 average rating, 226 reviews

Hobbit House of Pawling

DougRating, 5 stars3 weeks ago
The Hobbit House is as wonderful as one might imagine. Certainly the outside is charming and unique, but so too is the inside, filled with magical decorations, swords, maps, and even carved concrete ceilings! And the hot tub was preheated, and the water pressure was adequate, and the mountains and rock formations were awesome, and the bed was comfy, and our 30th anniversary will be a bright spot in our memories forever.
Superhost
Home in Shippan Point
4.94 out of 5 average rating, 116 reviews

OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC

DebraRating, 5 stars1 month ago
Victoria's place was wonderful! It was spacious and comfortable and gave our family plenty of room to spread out and enjoy our visit. Victoria was a very responsive host and made check in and check out stress free and easy! There was ample parking for our cars and the house was private - it was the "house behind the house" so we weren't subject to busy traffic noise on the street. (Got a little confusing for DoorDash drivers but we worked it out :D). I will book this same place next time I am up for an extended weekend with the family. Highly recommend!
Guest favorite
Home in Cold Spring
4.95 out of 5 average rating, 323 reviews

Hilltop Hideaway Forest Villa on 13 acres!

JillRating, 5 stars2 weeks ago
Paula was an exceptional host! She was always quick to respond and answered my many questions, before and during our stay. The house was fantastic for entertaining. It’s spacious and we loved the art! We would have loved to enjoy the beautiful decks, but it rained during most of our visit. We made a fire instead! The house has Sonas and we loved having music. The large windows are great and so were all the views. It made me feel like I was in a treehouse! I would highly recommend this Airbnb and host.
Superhost
Home in Sandy Hook
4.83 out of 5 average rating, 6 reviews

Serenity by Lakefront Cottage!

SabrinaRating, 5 stars3 weeks ago
The amazing place to spend with your partner, all clean, a beautiful view from the balcony, I loved it, I would come back more often
Top guest favorite
Home in Milford
5 out of 5 average rating, 96 reviews

Oceanfront Retreat: Modern Beach House

ShannonRating, 5 stars4 days ago
We had a relaxing overnight with our two pups! The bay/sound area is so peaceful. Our dogs enjoyed swimming before the tide came in and we kayaked along the shoreline. The inside was stunning and had everything you needed and more! We door dashed lobster rolls from the Bonfire Grille nearby (10/10) and ended the night in the hot tub! Coffee on the sunny patio was a great perk, too! Thanks again!!

House rentals with free parking

Guest favorite
Home in Fairfield
4.96 out of 5 average rating, 26 reviews

Once a Pond - time and stress slow down.

ShivaRating, 5 stars3 weeks ago
Spacious home with a nice outside area. Enjoyed coffee with birds and bunnies. Will stay here again.
Superhost
Home in Fairfield
4.85 out of 5 average rating, 86 reviews

Bright 3-bedroom house with ample parking & patio!

AlexaRating, 5 stars2 weeks ago
We have stayed at a number of Airbnbs and this is one we would definitely consider returning to in the future. The price was right and Alyson was super responsive to the couple of questions we had. Everything was really clean, the space was very comfortable, and we really liked the kitchen and the back family room area. There wasn't anything lacking in the kitchen and the fact that there was a washer and dryer really put it at the top of our list for return visits.
Top guest favorite
Home in Fairfield Beach
5 out of 5 average rating, 44 reviews

5 Minute Walk to Beach & Downtown Fairfield

FeliciaRating, 5 stars2 weeks ago
We had an amazing long weekend at Peter’s house. The house is great - close to the beach, and to an amazing playground if you have little kids like we do! He was so easy to work with, very responsive and flexible. Would definitely stay here again if we are ever back in this area!
Top guest favorite
Home in Milford
5 out of 5 average rating, 28 reviews

Bull Shark Bungalow-Walk to Beach, Pet Friendly

TeresaRating, 5 stars2 weeks ago
Steven’s place was fantastic! He was extremely responsive and flexible with both check-in and check-out, which was so helpful while traveling with kids. We stayed over Memorial Day weekend with our two small children and a dog, and his home was incredibly accommodating. The large backyard with a fire pit was perfect for making s’mores and spending evenings outside. The place was spotless - clean and tidy in every way. It was a wonderful stay for the whole family, and we’d happily come back again.
Guest favorite
Home in Milford
5 out of 5 average rating, 8 reviews

New build! 1 house from beach

MartinRating, 5 stars2 weeks ago
Immaculate, beautiful comfortable home on beach block with beautiful water views. Adriana and Robert were amazing, gracious hosts and couldn’t have been more responsive. Among our best Airbnb rentals ever!
Top guest favorite
Home in Black Rock
4.98 out of 5 average rating, 53 reviews

Stay at Black Rock Harbor

MRating, 5 stars1 week ago
Thank you, Allie! Your home was perfect for our stay! Bright, clean, nicely decorated and well-appointed for us to do a little cooking while staying! We loved being near the coast and our local friends showed us a beautiful loop walk along the waterfront and Ash Creek and including the delicious Harborview Cafe. We would love to visit again in the future.
Guest favorite
Home in Fairfield Beach
4.9 out of 5 average rating, 21 reviews

Seaside Home - Walk to Beach & Marina

PeterRating, 5 stars3 weeks ago
This was the second time staying at Angela’s place and it was a great experience, again! The location is great and the back yard is so peaceful and cozy. My family says it feels like it’s our Fairfield Home! I would highly recommend it! First Class!
Top guest favorite
Home in Milford
5 out of 5 average rating, 39 reviews

Lux cozy 2br/1ba Milford bungalow-walk to beach!

LeeannRating, 5 stars2 weeks ago
We loved our stay! The house and area were just as described and the list of recommendations Gracie shared with us was much appreciated- we did a lot that was on it and enjoyed everything!

House rentals with a pool

Guest favorite
Home in Stormville
4.94 out of 5 average rating, 179 reviews

Private Hudson Valley Country Retreat

MarkRating, 5 stars6 months ago
Place was perfect! Clean & made our Holiday stay in the beautiful Hudson Valley a wonderful experience. We loved the personal touches the house offered and we will be back
Guest favorite
Home in Stony Brook
4.93 out of 5 average rating, 535 reviews

Spacious Studio Apartment- near SBU

ElizabethRating, 5 stars1 week ago
Gabby’s apartment is exactly as described. It is in a great location. Very close to Stoney Brook Village. We enjoyed walking to get our morning coffee. The apartment was very well stocked and spotless. Gabby thought of everything we could have possibly needed. We hope to be back next year!
Top guest favorite
Home in Cheshire
5 out of 5 average rating, 135 reviews

Pool House

CindyRating, 5 stars2 weeks ago
The pool house is so cute and the outdoor patio is gorgeous and the perfect place to relax. Great place to stay if you want to stay near New Haven but also want to enjoy quiet away from the city. Sue is a responsive and very generous host!
Guest favorite
Home in The Hamptons
4.96 out of 5 average rating, 105 reviews

Stylish+Modern Cape w/Saltwater Pool-5min to Beach

JessicaRating, 5 stars1 week ago
Great spot in Hampton Bays! The house was as described and in a very cute and walkable neighborhood. Super close drive to the beach and a couple of local restaurants and eateries. Loved how private the spot felt too! David’s done a wonderful job with the backyard, so you get the comfort of having close neighbors without the intrusiveness. Pool was awesome. We definitely enjoyed it!
Guest favorite
Home in Stamford
4.96 out of 5 average rating, 250 reviews

Midcentury Modern ZenHouse Sculptor Studio

DianeRating, 5 stars1 month ago
Very relaxing and peaceful stay at the Zenhouse for me, my husband and 3 month old boy. The guest house was relatively spacious and had all the amenities needed to relax with tea/coffee and grill food. Some of the fixtures in the guest house are a bit dated (e.g. bathroom, heater, etc.) but are all perfectly functional. The property is expansive with beautiful trees, streams and walkways throughout. Olga greeted us with a wonderful welcome including of the history of the property. We also enjoyed spotting the geese, chipmunks and other animals that roam around the grounds. We would come again when during warmer weather to enjoy the pool next time.
Guest favorite
Home in North Fork
4.97 out of 5 average rating, 150 reviews

Secluded Farmhouse - Studio Apartment Style Unit

HelenaRating, 5 stars3 weeks ago
Jess’s place was lovely (and so was her recommendation for where to get a great egg sandwich!). We loved reading on the screened-in porch and being within walking distance of two wineries. Hope to be back next year!
Guest favorite
Home in Port Jefferson
4.92 out of 5 average rating, 124 reviews

Port Jefferson Convenient, Cozy and Chic!

DaleRating, 5 stars1 day ago
We we’re going to Port Jefferson for a family wedding. Our Airbnb was perfectly situated. There is a pool area that we never used because we just didn’t have time. But it looked very inviting. The town of Port Jefferson had plenty of nice restaurants and shops. This house was perfect for our situation. We had six adults, all family members.
Top guest favorite
Home in Pound Ridge
5 out of 5 average rating, 163 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

MollieRating, 5 stars2 weeks ago
Obsessed with this Airbnb! My husband, dog and I typically go to upstate NY or the Berkshires for long weekends but I came across this Airbnb as I had an event in westchester over the long weekend. Highly recommend! So much hiking, wonderful restaurants and so close to the city. My dog loved this property as well! Will be back.

Quick stats about house rentals in Bridgeport

  • Total rentals

    150 properties

  • Nightly prices starting at

    G$4,197 GYD before taxes and fees

  • Total number of reviews

    2.5K reviews

  • Family-friendly rentals

    70 properties are a good fit for families

  • Pet-friendly rentals

    30 properties allow pets

  • Rentals with a pool

    10 properties have a pool

Destinations to explore