Photo by Darrell Bumbala

Holiday Homes in Trumbull

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Check prices for these dates

Next weekend
7 Mar - 9 Mar
In two weeks
14 Mar - 16 Mar
In one month
28 Mar - 30 Mar
In two months
25 Apr - 27 Apr

Featured Holiday Homes in Trumbull

Escape to a Celebrity Chef's Waterfront Lake House
Interior

Escape to a Celebrity Chef's Waterfront Lake House

10.0 out of 10, Exceptional, (1)
Escape to a Celebrity Chef's Waterfront Lake House
Cozy Ocean Front Retreat with Private Beach!
Fridge, microwave, oven, stovetop

Cozy Ocean Front Retreat with Private Beach!

10.0 out of 10, Exceptional, (16)
"The views from this home are great - really enjoyed sunrises from the master bedroom. A very comfortable home with everything we needed. "
Cozy Ocean Front Retreat with Private Beach!
McAngel Haven: 5 mins from Yale
Fridge, microwave, oven, stovetop

McAngel Haven: 5 mins from Yale

9.8 out of 10, Exceptional, (10)
"Excellent to had a nice house like that "
The price is AU$901
includes taxes & fees
11 Mar - 12 Mar
McAngel Haven: 5 mins from Yale
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Property grounds

Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.

10.0 out of 10, Exceptional, (16)
"My time spent at the lake house with my family was unforgettable. Nestled along the serene shoreline, the house offered stunning lake views from every window. Mornings began with coffee on the spacious deck, watching the sun rise over the water. Days were filled with family fun. The house itself was cozy yet modern, with plush furnishings, a crackling fireplace, and a fully-equipped kitchen where we cooked meals together. Evenings were spent playing board games, hanging out by the fire pit. It...
Candlewood Lake - Family Getaway with direct lake access. 3775 sqft home.
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Terrace/patio

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Lake house cozy to relax with a family. 6 bedroom very spacious house.
Historic Hideaway with Lake Access!
Fridge, microwave, oven, stovetop

Historic Hideaway with Lake Access!

9.6 out of 10, Exceptional, (14)
"We were in town for work for the week and found this site online. Great spot, nice a quiet. "
Historic Hideaway with Lake Access!
Bright Milford Beach House w/ Outdoor Shower
Property grounds

Bright Milford Beach House w/ Outdoor Shower

9.6 out of 10, Exceptional, (7)
"We had the best time! It was clean, good location, and the owner was wonderful! We even got to go the beach in December! We would definitely rent this place again!!"
Bright Milford Beach House w/ Outdoor Shower
Near Yale with Game Room
Fridge, microwave, oven, stovetop

Near Yale with Game Room

The price is AU$1,810
includes taxes & fees
11 Mar - 12 Mar
Near Yale with Game Room
Ranch style living at its best with country garden & patio!
Exterior

Ranch style living at its best with country garden & patio!

9.6 out of 10, Exceptional, (8)
"Host worked with me due to larger dog. Very accurate instructions and all amenities were very good. Will stay here again"
Ranch style living at its best with country garden & patio!
Walk to Beaches: Sunny East Haven Home w/ Grill
Beach nearby

Walk to Beaches: Sunny East Haven Home w/ Grill

2.0 star property
10.0 out of 10, Exceptional, (3)
"6 of us stayed here for a music festival. The location, fantastic! Ocean views, check. The bedding, the furniture, kitchen supplies....no amenity was overlooked. Happened to meet owner when were checking in. He was great. Couldn't have been more accomodating. Great great place for a few nights or longer. Wush we were here longer. "
Walk to Beaches: Sunny East Haven Home w/ Grill
Home on the sound
Beach

Home on the sound

8.6 out of 10, Excellent, (7)
"This was a greay stay and the property was really cute and cozy. It is an upstairs portion of a duplex "
Home on the sound
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Interior

Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends

10.0 out of 10, Exceptional, (46)
"The house was beautiful and a perfect place for our family to be at while visiting our daughter who is a student at Yale. We saw the sunrise over the ocean from our bedroom window. Wish we found this sooner!"
Beautiful, Spacious, Beachfront Home - Perfect for Entertaining Family & Friends
Spacious 18th Century Victorian Mansion - Sleep 16+ Large Group
Interior

Spacious 18th Century Victorian Mansion - Sleep 16+ Large Group

10.0 out of 10, Exceptional, (1)
"We had a lovely family gathering with 14 adults and a toddler - the house was perfect for a large family meal and had room for everyone. Lots of games, a pool table, and electric fireplace were great additions. Rick was very helpful and easy to communicate with. Convenient on site parking. As stated in listing, the bedrooms are on 2nd and 3rd floor, with grand/tall staircases. Overall it was a great place for our family to celebrate together!"
The price is AU$2,696
includes taxes & fees
3 Mar - 4 Mar
Spacious 18th Century Victorian Mansion - Sleep 16+ Large Group
Lakeview Estate - Chef's Kitchen - NYC Getaway
Property grounds

Lakeview Estate - Chef's Kitchen - NYC Getaway

9.8 out of 10, Exceptional, (25)
"Great place, great service!!"
Lakeview Estate - Chef's Kitchen - NYC Getaway
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Outdoor dining

Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

9.8 out of 10, Exceptional, (28)
"Our family's stay at Helen and Richie's property for the holidays was perfect. Waking up to views of the lake every morning, watching flocks of birds travel on the water and being surrounded by nature was all we could ask for. The house has all amenities provided in the kitchen, bathrooms etc. Location is convenient near shops, grocery, and restaurants in New Fairfield. The hosts were very responsive in communication and I appreciated them providing everything we needed. "
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Waterview House Walking Distance from Cove Beach
Terrace/patio

Waterview House Walking Distance from Cove Beach

9.0 out of 10, Wonderful, (18)
"This was a late holiday gathering of family members from St. Louis and Rye New York. Great and easy spot to get to. Pretty setting with the water view. I am sure in warmer seasons it be great spot for all the outside amenities. Six adults and one baby. Space nice set up. "
The price is AU$2,140
includes taxes & fees
27 Mar - 28 Mar
Waterview House Walking Distance from Cove Beach
Cheerful 4 bedrooms residential house.
Fridge, microwave, dishwasher, coffee/tea maker

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (26)
"The house was clean, comfortable, and kitchen was great. Only problem was stairs for my handicapped sister-too steep but possible. Manager very nice"
Cheerful 4 bedrooms residential house.
Charming Coastal Retreat Steps from the Beach!
Smart TV, fireplace, books, stereo

Charming Coastal Retreat Steps from the Beach!

9.8 out of 10, Exceptional, (31)
"The house was perfect for our multi generation gathering, spacious enough for all. The kitchen was well equipped for our cooking needs. The beds very comfortable. Would highly recommend it!"
Charming Coastal Retreat Steps from the Beach!
Lakeside luxury: beautiful, relaxing 4 bedroom home
Property grounds

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (18)
"We enjoyed the lovely view of the lake and our wonderful, brisk walks in the neighborhood. The spacious and well-appointed lake home was perfect of our family with young adult children. We loved this beautiful, comfortable and entertaining home on the lake and hope to return."
Lakeside luxury: beautiful, relaxing 4 bedroom home
Seaview Ave House-4BR/8PPL Retreat
Fridge, microwave, oven, stovetop

Seaview Ave House-4BR/8PPL Retreat

9.8 out of 10, Exceptional, (8)
"This was an awesome place to stay. Very clean and well kept. When I needed to get in touch for some last minute questions, the owner was very prompt and eager to help. I would definitely stay here again."
The price is AU$1,011
includes taxes & fees
27 Feb - 28 Feb
Seaview Ave House-4BR/8PPL Retreat
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.
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Other property types in Trumbull

Lakeside luxury: beautiful, relaxing 4 bedroom home
Property grounds

Lakeside luxury: beautiful, relaxing 4 bedroom home

10.0 out of 10, Exceptional, (18)
"We enjoyed the lovely view of the lake and our wonderful, brisk walks in the neighborhood. The spacious and well-appointed lake home was perfect of our family with young adult children. We loved this beautiful, comfortable and entertaining home on the lake and hope to return."
Lakeside luxury: beautiful, relaxing 4 bedroom home
Lake house cozy to relax with a family. 6 bedroom very spacious house.
Terrace/patio

Lake house cozy to relax with a family. 6 bedroom very spacious house.

Lake house cozy to relax with a family. 6 bedroom very spacious house.
Charming 1-bedroom apartment in delightful Trumbull with AC and many amenities
Private kitchen

Charming 1-bedroom apartment in delightful Trumbull with AC and many amenities

Charming 1-bedroom apartment in delightful Trumbull with AC and many amenities
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.