
House holiday rentals in Trumbull
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Top-rated house rentals in Trumbull
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Holiday rentals for every style
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Popular amenities for house rentals in Trumbull
House rentals with a pool

The Getaway-HOST & Co.
I absolutely enjoyed my weekend here. The home is beautiful. Everything you could possibly need was provided In the home. Everything was clean, and neat. House is filled with light. The pool and hot tub were enjoyable. The host were amazing and had great communication, assisted us when needed right away. I would highly recommend staying here, and they are pet friendly which is always a plus for me. The yard is fenced in. Which made it easy to let the dog out, and great for the dog to explore. A++++ Will probably be back sometime In the future.

Private Hudson Valley Country Retreat
Our second time here. Great spot for our family of 4, and Sandy is very responsive

Pool House
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!

Midcentury Modern ZenHouse Sculptor Studio
Truly one of a kind property. Relaxing, calm, extremely responsive and helpful host. If you are looking to get out of the city or just need some time away to think, look no further. 10/10.

Secluded Farmhouse - Studio Apartment Style Unit
Great location, private and comfortable. Close to wineries and breweries. Very clean and convenient. I highly recommend.

Port Jefferson Convenient, Cozy and Chic!
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.

Peaceful Light-Filled Guesthouse 1 Hour From NYC
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.

Waterview+Pool, FreeForDogs! Kayaks/PingPong/Bikes
We had a wonderful two day stay at Roger and Amy’s place. It was fantastic- such a beautiful, inviting home. Our kids had a blast in the heated pool- we could barely get them to come out despite it being under 60 degrees out! The kitchen was stocked with more than just kitchen basics- the spice cabinet had soo many different choices ! It was probably the most perfect AirBnb experience I’ve had and we travel plenty.
Weekly house rentals

Bobby's Beach Bungalow
We very much lived our stay in this beautiful home. The location eas perfect for our visit and there are lots of walkable shops and eats nearby. would definitely stay again when in the area.

Adorable Beach House on LI Sound
Such a beautiful place! So much to walk to and had great views of the ocean. Very clean and tidy space with everything you would need! Eileen was very responsive and super friendly. Defiantly coming back!

Bull Shark Bungalow-Walk to Beach, Pet Friendly
Perfect for a weekend stay with friends. The dogs had a great fenced in back yard to run around in, awesome fire pit and outdoor space as a whole. The house was cute and was perfect for 5 of us. However, the 3rd bedroom does not have a door, only curtains.

Beautiful, Cozy basement space
Rachel and I were in Bridgeport for a wedding and booked Hurberts.He is a lovely host very responsive clean room and very organized . We will recommend this place to anybody be rest assured you are safe and you will definitely feel at home !!!

Remodeled Cozy Country Cape
Karen's home was a great place to stay for our 10 year college reunion. Plenty of space for 2 couples and great location.

Westport Deco HAUS /5 min to Town /10 min to Beach
great location and loved the backyard

Westville Schoolhouse by Stephanie and Damian
Where to start! I could write an epistle about my stay but I'll keep it short and sweet. What an absolutely beautiful and stunning home! from the moment I arrived I felt right at home. Stephanie and her husband put a lot of thought into every detail of their home and they went above and beyond to ensure our stay was perfect. I wish I had an extra week! I appreciated how central the location is but still allows you to feel as though you are in a private oasis. I can't wait to be back in New Haven to rent from Stephanie again! you are a super host for a reason :) Thanks for making your home my home. My family and I truly enjoyed our stay. Already planning my next trip!

Modern Beach Mood!
Great spot in a great location! Cole was flexible and communicative. Would love to stay again next time I’m in Milford!
Private house rentals

Bright 3-bedroom house with ample parking & patio!
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.

HGTV renovation! Steps to shops & water | Firepit!
We had a great stay! Home was clean and as described. Host was responsive and very helpful during our stay. Would highly recommend

New build! 1 house from beach
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!

Lakeview Estate - Chef's Kitchen - NYC Getaway
This house was wonderful as I would definitely stay there again and recommend it to family and friends. The views from the balconies and windows were amazing! The house was absolutely beautiful and super clean. The location was secluded but still near shops and restaurants. We loved our stay!

Cape on the Water
Jim’s place was perfect for our stay. The house was exactly as advertised. Our favorite part was the beautiful view of the salt marsh in back with lots of birds to watch.

Oceanfront Retreat: Modern Beach House
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!!

Cheerful 4 bedroom home with all the updates
Stayed here for our sins wedding. Location was perfect. Very cozy, comfortable beds and quiet neighborhood. We felt right at home.

3BD w/ Hot Tub + FRER EV | Close 2 Beach +Yale
Wow, I don’t even know where to start! My family and I just had the most incredible time celebrating my niece's 21st birthday. From the moment we arrived, Annie blew us away as the ultimate host! The house was decked out with beautiful decorations that truly made the surprise unforgettable. And guess what? She even had a magnificent birthday cake waiting for us! The house itself was absolutely gorgeous and so inviting. We felt right at home with an abundance of linens, towels, and toiletries—perfect for a group of five women! The jacuzzi was a dream, and the grill was all set for us to fire up some delicious meals. Plus, the kitchen was stocked with all the essentials and some delightful extras! Annie was always quick to respond to our questions, which made everything even easier. We were thrilled to find beach necessities already available, so we didn’t have to worry about bringing our own. There’s so much more I could rave about, but overall, this stay was amazing.
Quick stats about house rentals in Trumbull
Total rentals
30 properties
Nightly prices starting at
₹3,443 before taxes and fees
Total number of reviews
370 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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- Columbia University
- Jones Beach
- Fairfield Beach
- Southampton Beach
- Yale University
- Rye Beach
- Citi Field
- Yankee Stadium
- Gilgo Beach
- Rye Playland Beach
- USTA Billie Jean King National Tennis Center
- Bronx Zoo
- Cooper's Beach, Southampton
- Point Lookout Beach District Park
- Robert Moses State Park
- Astoria Park
- Walnut Public Beach
- Shinnecock Hills Golf Club
- TPC River Highlands
- Dunewood
- Bethpage State Park
- Thunder Ridge Ski Area
- Woodmont Beach
- Rye Town Beach