
Holiday houses in Trumbull
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Trumbull
Guests agree: these stays are highly rated for location, cleanliness and more.

2 BRm Suite; Ktchn; Livng area; wash/dryr; Private
Fully accessorized, large (919 sq ft) beautiful suburban space with bedroom (queen); convertible Murphy bed (queen), in-room sitting area/large screen TV, kitchenette; 2nd room: bedroom (queen) with living space / large screen TV; private full bath; in-suite washer/dryer; private entry to suite (front door; up 1 flight of stairs). Includes light continental breakfast. Owners on property. Off street parking. Train station a mile away (NYC: 70 min). 2 miles to beach. Easy walk to Fairfield U.

The Pond Mill Retreat w/ 2 Bdrms & Pool
Catch up on a little work or simply unwind. Everything is waiting for you in this cozy, yet functional space surrounded by a beautiful wooded area with pond. Your private entrance accommodations include a finished, walk-out lower-level apartment (~730 sq ft) containing thoughtfully appointed bedrooms, living room, kitchen, and full bathroom. Experience solitude while enjoying the convenience to Rt 15, I-95, & Boston Post Rd destinations. And if you require assistance, we live right upstairs.

Huckleberry Quarters, the Cozy Redding Retreat.
Now is the time to book your SPRING STAYCATION at the Huckleberry Quarters, a beautifully appointed studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A peaceful country getaway to enjoy any season, a writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

The ARLO - Walk to Brewery & Restaurants
Newly remodeled and designed, The ARLO combines a seamless blend of luxury & comfort for your family. Walking distance to Dockside brewery & stand-out local restaurants, while only 1 mile from the beautiful Walnut Beach. Enjoy a thoughtful & comfortably designed living room, cook in the chef-style kitchen, indoor/outdoor living with a game room and fully-fenced yard. -Less than 2 minutes to The Tyde wedding venue. -15 min to Fairfield U & Sacred Heart -15 min to YALE -0.2 miles off I-95

The River Loft
Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

The Cottage on Babbling Brook
A cozy, rustic cottage beautifully overlooking Wimsink Brook. Custom designed & handcrafted woodwork throughout the home. An all around great spot for families and friends. A magical, peaceful and relaxing space. Conveniently located on the Connecticut/New York border, just a 1 ½ hour drive or metro north from NYC. The area is a prime location, as it offers some of the most stunning and scenic hikes & drives in the country. Only a 10 minute drive from Kent, New Milford or Pawling.

Comfortable home away from home- near everything
Price includes Airbnb fees. Cozy, pet-friendly cottage in a peaceful setting just 70 miles from NYC and minutes from I-84 (Exit 8 or 9). This clean & comfortable retreat features 3 bedrooms (2 queens, 1 full), and pull-out couch. Portable A/C's in summer, and fireplace for cozy nights. The greenhouse adds plenty of natural light, the yard is perfect for kids, the front deck is great for morning coffee, and the gas grill great for cooking out. High-speed WiFi and 3 smart TVs.

The Cove Cabin
An original Candlewood style cabin. The house has been updated to offer all modern comforts. It features a large fireplace in the living room, porch over looking the lake, central heat and air conditioning and a fully equipped cook's kitchen. It is on the northern most part of Candlewood Lake with direct, private water access from the shore or the dock. A foam lily pad, two SUP, and two inflatable two person kayaks are available for use from May 1 to November 1..

Sunny Fairfield Studio Apartment
Enjoy this sunny, newly-renovated, modern Fairfield studio apartment, located in the carriage building of a historic early 1900's house. Great for an individual, couple, or family. Well situated, a short drive to Sacred Heart & Fairfield Universities, downtown Fairfield and the beach, Silverman's Farm and other Easton farms for apple picking, petting zoos, and the like, and Fairfield Metro Station for a 1 hour train ride to NYC.

Cozy Colonial - Private Hot Tub & Entire House
The way Airbnb was meant to be, something special... a home away from home. No long rule book, just be respectful. Come and stay in this cozy colonial home centrally located in Stratford CT. Walk to the park, soak in the spa, sip tea, listen to music, play games, and relax. Less than 10 minutes from some of the best CT has to offer - beaches, shopping, restaurants, grocery, entertainment, hiking, train to NYC / Yale, and more.

Cozy Cottage with Fire Pit, near Beach
Escape to Fairfield Cottage, a stylish 3-bed, 2-bath retreat 90 mins from NYC. Comfortably sleeping 8, this sun-drenched home features a private patio with a fire pit, a fully equipped kitchen, and two fireplaces. Perfect for families and just 3 miles from the beach, it's your ideal getaway for relaxation and connection. Enjoy a dedicated workspace, fast Wi-Fi, and numerous family-friendly amenities for an unforgettable stay.

Midcentury Lakeside Guest Suite
Private guest studio suite in a beautiful, midcentury lakeside home. Built in 1957, this home on a quiet residential street is a unique piece of modern architecture around a serene lake in suburban Connecticut. It is walkable from the nearby railway station, and it is close to West Haven's picturesque beaches, and a short drive from downtown New Haven.
Popular amenities for Trumbull holiday rentals
Other great holiday rentals in Trumbull

Cozy Private Studio | Easy Transit & Beaches

Beautiful, clean and quiet place to relax

Designer Treehouse with Spa Bath

Cheerful 4 bedroom home with all the updates.

Newly Restored Cottage on River

Waterfront Getaway - Norwalk, CT

Cozy Studio in Bridgeport

Lux Modern Loft ,Ricport Studio 1 Peaceful Stay
When is the best time to visit Trumbull?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $176 NZD | $175 NZD | $186 NZD | $208 NZD | $249 NZD | $247 NZD | $213 NZD | $292 NZD | $254 NZD | $242 NZD | $200 NZD | $200 NZD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Frequently Asked Questions
How much does it cost to stay in house rentals in Trumbull?
Experience the best of Trumbull with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there vacation rentals with a dedicated workspace in Trumbull?
Yes! Work meets play with ease at over 20 vacation rentals in Trumbull featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there family-friendly vacation rentals in Trumbull?
Trumbull has more than 10 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Are there pet-friendly vacation rentals in Trumbull?
Four-legged friends are welcome in Trumbull. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Trumbull have air conditioning?
Absolutely! We offer over 20 house rentals with air conditioning in Trumbull. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Trumbull have wifi?
Absolutely! We offer over 30 house rentals with wifi in Trumbull. Enjoy a tailored experience with all the comforts you desire.
Quick stats about holiday rentals in Trumbull

Total holiday rentals
Explore 40 holiday rentals in Trumbull

Nightly prices starting at
Trumbull holiday rentals start at $67 NZD per night before taxes and fees

Verified guest reviews
Over 960 verified reviews to help you choose

Family-friendly holiday rentals
10 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Trumbull holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ grill and Laptop-friendly workspace across Trumbull rentals

4.8 Average rating
Trumbull stays are highly rated by guests—averaging 4.8 out of 5!
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- Columbia University
- Yale University
- Yankee Stadium
- Jones Beach
- Citi Field
- Cooper's Beach, Southampton
- USTA Billie Jean King National Tennis Center
- Thunder Ridge Ski Area
- Astoria Park
- Fairfield Beach
- Bronx Zoo
- Southampton Beach
- Robert Moses State Park Beach
- Sunken Meadow State Park
- Jones Beach State Park
- Kent Falls State Park
- Hammonasset Beach State Park
- UBS Arena
- Mohawk Mountain Ski Area
- Riverside Park
- Yale University Art Gallery
- Bear Mountain State Park
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park





