House vacation rentals in Bridgeport

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Popular amenities for Bridgeport house rentals

House rentals with a pool

Guest favourite
Home in North Fork
4.97 out of 5 average rating, 203 reviews

Private Oasis W/Stunning Vinyard and Pool Views

KimRating, 5 stars4 months ago
This is the 2nd Thanksgiving weekend we spent at Deeanna's. Her home is beautiful, comfortable and each detail is thought though in the best way. Deeanna went above and beyond to accommodate my family and we are so grateful to her. The kitchen is perfection and the bedrooms are lovely and comfortable. The scenery and views are breathtaking. Overall, this home is a total gem. Thank you, Deeanna! We hope to come back next year!
Guest favourite
Home in Stormville
4.94 out of 5 average rating, 178 reviews

Private Hudson Valley Country Retreat

MarkRating, 5 stars4 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 favourite
Home in Stony Brook
4.93 out of 5 average rating, 522 reviews

Spacious Studio Apartment- near SBU

JaimeRating, 5 stars3 weeks ago
Gaby’s place was clean and comfortable! She is very kind and it was exactly what we needed for the week. Her check in instructions and directions were thorough and the home is in a beautiful area. Already have our next stay booked :)
Top guest favourite
Home in Cheshire
5 out of 5 average rating, 132 reviews

Pool House

MelissaRating, 5 stars3 months ago
This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.
Top guest favourite
Home in Monroe
4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars1 month ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
Guest favourite
Home in Stamford
4.96 out of 5 average rating, 246 reviews

Midcentury Modern ZenHouse Sculptor Studio

KayRating, 5 stars1 month ago
We had a lovely stay. Olga really cares about her guests' comfort. The setting is beautiful and feels secluded, even though the house is minutes from markets and restaurants. The bed is very comfortable. We were there in winter, so we didn't use the pool, but did have some sweet encounters with the resident geese and swan.
Superhost
Home in Fairfield
4.71 out of 5 average rating, 7 reviews

Modern Beach Area Vacation Home With Pool

VRating, 5 stars16 months ago
We were all very happy with the check-in/check-out. Instructions were clear and host left helpful information. Beds were quite comfortable. More than enough space for all. Laundry room was a plus. Easy to access town & beach. Lovely place - quiet - clean. Would definitely book again.
Top guest favourite
Home in North Fork
4.97 out of 5 average rating, 145 reviews

Secluded Farmhouse - Studio Apartment Style Unit

JamieRating, 5 stars1 week ago
We had a great stay at Jess and Zack’s place for my birthday weekend on the North Fork! They provided clear directions ahead of time on how to find their place and how to check in. We were greeted by the sweetest pup. The space was spotless and very comfortable. We had a fire in the fire pit one night and that was excellent. It’s super close to lots of great restaurants and wineries! I would recommend their place to anyone looking for a quiet and peaceful getaway!

Weekly house rentals

Superhost
Home in Westbrook
4.85 out of 5 average rating, 192 reviews

Family-Friendly Cottage by The Shore

HeatherRating, 5 stars1 week ago
Adorable, cozy and comfortable! Short drive to the beach and plenty of restaurant options. Both Westbrook and Clifton are cute New England towns!
Guest favourite
Home in Ridgefield
4.95 out of 5 average rating, 40 reviews

Modern, Charming New England Pool Home Getaway

MelissaRating, 5 stars1 month ago
We had a great stay at this home. The purpose was for family to gather for an 85th birthday and it was perfect. The home was well stocked with all we needed. It was clean, beautifully decorated and so comfortable. We had plenty of space to all gather together and everyone also had their own private space. We would absolutely rent again. Thank you!!
Superhost
Home in White Plains
4.88 out of 5 average rating, 8 reviews

Indigo Inn III -A Retro Modern Cove White Plains

ShannonRating, 5 stars6 months ago
Great space. Wonderful communication with host regarding any questions we had. Host was quick to respond. Very happy with the stay, would rent again.
Top guest favourite
Home in Cold Spring
4.89 out of 5 average rating, 45 reviews

Cabin with a View

TerriRating, 5 stars3 days ago
Ellen’s place was beautiful and cozy. The kitchen worked perfectly and even though it was April it was still a bit chilly so the wood stove was a welcome amenity. The shower was great and there was a soaking tub. It was quiet and beautiful. We like all the art and it was very homey.
Superhost
Home in Pound Ridge
4.85 out of 5 average rating, 48 reviews

1840Farmhouse, 65"OLED4k, firepit, 3x4ktvs, 3acres

GailRating, 5 stars1 month ago
Charming place, comfortable and spacious enough for time alone. Kitchen was great, beds are comfortable , plenty of hot water, the art was interesting, we were warm and felt very happy to be there.
Guest favourite
Home in Clinton
4.97 out of 5 average rating, 122 reviews

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON

DavidRating, 5 stars3 weeks ago
Great little weekend getaway. House had everything you could need. TVs everywhere which was great for everyone to watch what they want/like. Kitchen was great. We did have a small inconvenience that Charlotte got back to us right away on. It did not impact us much. Instructions were clear. Truly could walk right on the beach.
Top guest favourite
Home in Cos Cob
5 out of 5 average rating, 16 reviews

GREENWICH HOUSE WITH NYC FLAIR/CLOSE TO BEACH /NYC

AnishRating, 5 stars1 month ago
This is our 2nd review Victoria’s properties and we just want to reiterate how special of a landlord Victoria is. The best. I cannot recommend her properties enough if you are in need of a Greenwich rental like we were.
Guest favourite
Home in Madison
4.87 out of 5 average rating, 23 reviews

Historic Beachside Glamour

GretchenRating, 5 stars6 months ago
A lovely cottage on a quiet street (at least in the fall!). The interior is just beautiful with all the wood floors, walls, ceilings. The kitchen was - unusual! Clearly they had to retrofit an old home to accommodate modern appliances, but all worked well.

Private house rentals

Superhost
Home in Trumbull
4.87 out of 5 average rating, 38 reviews

Beautiful House to relax with the Family.

KassandraRating, 5 stars4 months ago
One of the best airbnbs I’ve stayed at! The house is so beautiful and clean! Beds are extremely comfortable and the views of the lake is stunning!! Thanks so much again for a wonderful stay with my family!
Top guest favourite
Home in Wading River
4.96 out of 5 average rating, 499 reviews

Your Zen Retreat

DanielleRating, 5 stars1 month ago
Myself and a few friends stayed here to celebrate a 40th birthday and we all loved it! The space is so unique yet still cozy and very relaxing. We were able to cook easily in the fully stocked kitchen all of the bedrooms were comfortable. Spent a majority of our time just hanging in the living room, but did get around to utilizing the hot tub. Would highly recommend this place for a nice relaxing weekend away.
Top guest favourite
Home in Bedford
5 out of 5 average rating, 26 reviews

The Waterside Home - Pool, Tennis, Sauna & Golf

CateRating, 5 stars4 months ago
We were fortunate to spend several months at the Waterside Home with our two children and our dog during our house renovation and couldn’t have asked for a more charming and peaceful spot. Jonathan is a wonderful host and was always responsive. Pictures cannot begin to do justice to the spectacular landscaping, the mature trees and paths carved through cultivated wildflower meadows. We loved playing tennis and pickleball with our kids. While given privacy, we all appreciated the well-cherished grounds. Inside, there was plenty of room to accommodate our family. It’s well-furnished, charming and functional and very much like a home rather than a rental house. The kitchen has everthing we needed. The primary suite in particular is lovely and large with stunning views over the reservoir. Last, the location is perfect within a few easy minutes of Katonah’s cute shops and restaurants and near 684 yet completely quiet, secure and tranquil. Thank you Jonathan for a perfect stay!
Guest favourite
Home in East Haven
4.89 out of 5 average rating, 100 reviews

Welcome To Piper's Rest

DavidRating, 5 stars1 month ago
Easy to work with. Close to the water too. Great place to stay at?
Guest favourite
Home in North Salem
4.94 out of 5 average rating, 31 reviews

North Salem Home with Pool & Great Yard

DanielleRating, 5 stars6 months ago
This was a lovely home. Very easy getting inside. Everything was exactly as listed, pictured and described. We felt so cozy and welcomed by Susan. The house had everything you could possibly need to make your stay easy and convenient and was very clean. I had a few questions during our visit and Susan was extremely responsive and so kind. I highly recommend this home. The beds were very comfortable. Showers were very nice and had great water pressure and nice hot water. We truly felt at home and we're beyond satisfied. I highly recommend this home for anyone need of an Airbnb in the area. Lovely home and property.
Guest favourite
Home in Carmel Hamlet
4.93 out of 5 average rating, 73 reviews

Country getaway with pool and hot tub on 9 acres

VinnyRating, 5 stars2 months ago
We loved our stay in Calum's Airbnb! It is a short commute from NYC and conveniently located between two main areas with plenty of grocery store and restaurant options. The home itself is well equipped with an amazing kitchen and many board games - so we were always entertained.
Guest favourite
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars3 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!
Superhost
Home in Ridgefield
4.81 out of 5 average rating, 21 reviews

Log House, sits on 3acres. A retired mini farm.

TaylorRating, 5 stars1 week ago
Great stay! Tough to heat the downstairs if it’s cold, but a great cozy space nonetheless. Would definitely recommend :)

Quick stats about house rentals in Bridgeport

  • Total rentals

    150 properties

  • Nightly prices starting at

    $28 CAD 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