Book Holiday Homes in Trumbull

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Trumbull

Historic Connecticut Home w/ Grill & Spacious Yard

Historic Connecticut Home w/ Grill & Spacious Yard

Weston
When you stay at this vacation home in Weston, you'll be within a 10-minute drive of Wilton Historical Society and Westport Historical Society.
Historic Connecticut Home w/ Grill & Spacious Yard
Lakeside luxury: beautiful, relaxing 4 bedroom home

Lakeside luxury: beautiful, relaxing 4 bedroom home

Trumbull
With a stay at this vacation home in Trumbull, you'll be within a 10-minute drive of Northeast Medical Group and Roosevelt Forest.
Lakeside luxury: beautiful, relaxing 4 bedroom home
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake

Danbury
Located in Danbury, this vacation home is on the waterfront, a 1-minute drive from Candlewood Lake and 7 minutes from Candlewood Plaza Shopping Center.
Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake
Save an average of 15% on thousands of hotels when you're signed in
Business or Weekend escape

Business or Weekend escape

Stratford
The price is AU$218 per night from 7 Apr to 8 Apr
AU$218
includes taxes & fees
7 Apr - 8 Apr
Located in Stratford, this vacation home is within a 5-minute drive of Perry House and Stratford Historical Society Capt David Judson House.
Business or Weekend escape
Cheerful 4 bedrooms residential house.

Cheerful 4 bedrooms residential house.

Bridgeport
When you a stay at this vacation home in Bridgeport, you'll be by the sea, just steps from Bridgeport Downtown South Historic District and University of ...
Cheerful 4 bedrooms residential house.
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger

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

New Fairfield
Located in New Fairfield, this vacation home is on the waterfront, a 1-minute drive from Candlewood Lake and 7 minutes from Squantz Pond State Park.
Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger
Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown

Westport
Located in Westport, this vacation home is within a 5-minute drive of Westport Historical Society and Levitt Pavilion.
Main Street Westport, walk to shops, dining, downtown
7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather

New Haven
With a stay at this vacation home in New Haven (West New Haven), you'll be within a 15-minute drive of Yale University and Quinnipiac University.
7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather
Beautiful 4BR Beach House with Private Beach Access.

Beautiful 4BR Beach House with Private Beach Access.

Branford
With a stay at this vacation home, you'll be centrally located in Branford, within a 15-minute drive of Yale University and Stony Creek - Thimble Islands Historic ...
Beautiful 4BR Beach House with Private Beach Access.
Don't see what you're looking for?
See all available properties in Trumbull
View all properties
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.

Trumbull Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Trumbull vacation homes are the perfect way for you to wing it.

Holiday houses in Trumbull let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Trumbull in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Trumbull adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Trumbull with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Trumbull vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Trumbull Holiday Homes essential information

Accommodation
430 Holiday Homes
Lowest Price
AU$156
Highest Price
AU$278
Popular accommodation
Historic Connecticut Home w/ Grill & Spacious Yard, Lakeside luxury: beautiful, relaxing 4 bedroom home, Charming Direct Waterfront Home w/Panoramic Views and Hot Tub on Candlewood Lake, Business or Weekend escape, Cheerful 4 bedrooms residential house., Direct Lakefront Living - Floating Dock, Boat Watching, Kayaks, & EV Charger, Main Street Westport, walk to shops, dining, downtown, 7Mins to Yale I ENTIRE HOUSE I Large fenced yard I King bed I 3BR I Group Gather, Beautiful 4BR Beach House with Private Beach Access.

Top trending hotels in Trumbull

Trumbull Marriott Shelton

Trumbull Marriott Shelton

3.5 out of 5
180 Hawley Ln, Trumbull, CT
Fully refundableReserve now, pay when you stay
The price is AU$278 per night from 15 Apr to 16 Apr
AU$278
includes taxes & fees
15 Apr - 16 Apr
Located in Trumbull, Trumbull Marriott Shelton is in the suburbs, within a 5-minute drive of Northeast Medical Group and Roosevelt Forest.
Trumbull Marriott Shelton
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is AU$216 per night from 20 Apr to 21 Apr
AU$216
includes taxes & fees
20 Apr - 21 Apr
New Haven Hotel is centrally located in New Haven, a 4-minute walk from Shubert Theater and 5 minutes by foot from New Haven Green.
New Haven Hotel
Clarion Inn

Clarion Inn

3 out of 5
201 Washington Avenue, North Haven, CT
Fully refundableReserve now, pay when you stay
The price is AU$156 per night from 6 Apr to 7 Apr
AU$156
includes taxes & fees
6 Apr - 7 Apr
With a stay at Clarion Inn in North Haven, you'll be within a 15-minute drive of Yale University and Quinnipiac University.
Clarion Inn
Save an average of 15% on thousands of hotels when you're signed in
EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
Fully refundable
The price is AU$214 per night from 6 Apr to 7 Apr
AU$214
includes taxes & fees
6 Apr - 7 Apr
Located in Norwalk, EVEN Hotel Norwalk by IHG is in the business district, within a 5-minute drive of Caldor Shopping Center and Gateway Shopping Center.
EVEN Hotel Norwalk by IHG
Don't see what you're looking for?
See all available properties in Trumbull
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.