Photo by Darrell Bumbala

Holiday Homes in Trumbull

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks
In one month
In two months

Featured Holiday Homes in Trumbull

Our top choices for Trumbull holiday homes

Cozy 2 bedroom home located minutes from downtown

9.6 out of 10, Exceptional, (29)
"Perfect stay for the Yale-Harvard game. "
Cozy 2 bedroom home located minutes from downtown

Cozy Home Near New Haven

10.0 out of 10, Exceptional, (1)
"So comfy for the dog and I for a night. Just what we needed!"
The price is AU$249
includes taxes & fees
9 Sept - 10 Sept
Cozy Home Near New Haven

Modern Beach Home - Waterview, close to restaurants, universities and hospitals

10.0 out of 10, Exceptional, (1)
"The check in process was very easy. The home was airy and bright. My family and I felt the peace and relaxation of the home. The kitchen was large and clean."
Modern Beach Home - Waterview, close to restaurants, universities and hospitals

Stareway to Heaven Su

10.0 out of 10, Exceptional, (6)
"We stayed with family at this lovely home for my son’s graduation and Mother’s Day. The home is even nicer than the pictures- everything is top notch. It’s one block from a nice beach with lovely views from many of the rooms. We would love to come back and stay! "
Stareway to Heaven Su

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

10.0 out of 10, Exceptional, (123)
"We had a magical stay in this truly enchanting home the beds were comfortable. The kitchen well equipt for entertaining a large crowd. The fire place and piano were the backdrop for many intimate moments. The gardens were beautiful with azaleas and many perennials. The location directly across from the beach allowed for many walks and playtime together and the waves sung us to sleep at night. We would love to make a new family tradition for visiting here again and again."
Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Beach Bungalow, walk to beach, private backyard

10.0 out of 10, Exceptional, (3)
"The property was perfect for all of us. It was in a quiet neighborhood and great location."
Beach Bungalow, walk to beach, private backyard

Charming 3-bedroom house with WiFi, AC in serene Fairfield

9.6 out of 10, Exceptional, (5)
"Thank you for the stay!"
Charming 3-bedroom house with WiFi, AC in serene Fairfield

Business or Weekend escape

9.2 out of 10, Wonderful, (44)
"Very nice owner with great communication. "
The price is AU$231
includes taxes & fees
14 Sept - 15 Sept
Business or Weekend escape

Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

9.8 out of 10, Exceptional, (66)
"We very much enjoyed our stay and were pleasantly surprised by how great the views were from practically every room in the house. Check-in was very simple and there were many nice touches awaiting us at the property. "
Exclusive Weekend Summer Sale here Waterfront Beach Home🏖️Hot Tub+Stunning Views

Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

10.0 out of 10, Exceptional, (44)
"Wonderful property with a great location."
Candlewood Lakefront 3bd/ 2 bath house w/ 180 degree views!

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (33)
"House was very clean and maintained. We needed to check in a day later and the host was very accommodating. Overall a great place to stay! "
Cheerful 4 bedrooms residential house.

Family Gem on Dyer Street

The price is AU$1,436
includes taxes & fees
24 Aug - 25 Aug
Family Gem on Dyer Street

Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

10.0 out of 10, Exceptional, (1)
Lakeside/Sleeps20/HotTub/GameRoom/2Acres/Firepit

Cozy 3 bedroom minutes from Yale and the beach

8.0 out of 10, Very good, (4)
"The inside was very clean, the back patio/garden area is cute, but the pool was green by day two. Overall we enjoyed our time here"
Cozy 3 bedroom minutes from Yale and the beach

Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

10.0 out of 10, Exceptional, (11)
"The house worked very well for our family holiday. Very clean, had everything we needed "
Private Beautiful Home - Family Friendly - 1 min. Walk to Candlewood Lake

Soothing Carriage House with Hot Tub in charming Stratford

10.0 out of 10, Exceptional, (3)
"Check in was super simple and easy. Kitchen area was so clean and neat. Overall stay was a wonderful experience. "
Soothing Carriage House with Hot Tub in charming Stratford

Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

10.0 out of 10, Exceptional, (26)
"The house was very clean and comfortable with really nice seating inside and out with great views of the lake. Our family really enjoyed"
Beautiful Renovated Direct Waterfront Candlewood Lake Home~Views~Weekly Discount

Lordship Charmer HAS IT ALL! Comfortable stay, accessible, family friendly!

9.8 out of 10, Exceptional, (10)
"Very nice place close to the beach and nice restaurant. The host was very nice and did a very good banana cake."
Lordship Charmer HAS IT ALL! Comfortable stay, accessible, family friendly!

Litchfield County Four Season Country Paradise

9.6 out of 10, Exceptional, (47)
"Overall rating 5/5. I would recommend this home to other families and would stay again. "
Litchfield County Four Season Country Paradise

3-bedroom house just walking distance from Yale and Downtown

The price is AU$661
includes taxes & fees
25 Aug - 26 Aug
3-bedroom house just walking distance from Yale and Downtown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Trumbull Hotel Reviews