Holiday rentals in Trumbull

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Top-rated holiday rentals in Trumbull

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A spacious bedroom features a queen-sized bed with a light-colored quilt. Two elegant armchairs are positioned around a glass-topped table. Natural light floods in through multiple windows adorned with lace curtains, providing views of the verdant surroundings.
Guest suite in Fairfield
4.93 out of 5 average rating, 179 reviews

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Fully accessorized, large (1,255 sq ft) beautiful suburban space consisting of bedroom (queen), an exclusive-use living room/extra bedroom with twin pull-out bed, private full bath; in-unit washer/dryer; exclusive use of kitchen (was the main kitchen of the house); private entrance to space thru side door of the house. Two large-screen TVs. Unit on the ground floor of a 3 story home. Owners on property. Train station about a mile away (NYC: 70 minutes). Easy walk to Fairfield University.

Top guest favourite
An expansive patio extends towards the shimmering waters of Long Island Sound, featuring lounge chairs and a dining table with an umbrella. Decorative planters and lanterns are arranged along the patio edge, complementing the serene waterfront view.
Flat in Milford
4.97 out of 5 average rating, 618 reviews

Water front studio apartment with fireplace.

This is a beautifully appointed studio apartment located off the patio level of a water front home. Guests enjoy a large private patio over looking gorgeous sweeping views of Long Island Sound. A private entrance and off street parking. The amazing views and amenities make this space the perfect romantic getaway! Close to I95 and Metro North railroad. Ten minutes to great dining in downtown Milford. A true waterfront oasis! Come and experience this beautiful retreat! You won't be disappointed!

Top guest favourite
A wooden porch is visible, featuring two black chairs and an orange table. Potted flowers add color on either side, with a stone pathway leading into the surrounding greenery. The gray siding of the building complements the outdoor seating area.
Flat in Redding
4.94 out of 5 average rating, 502 reviews

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.

Top guest favourite
A comfortable living room is featured, with a gray sofa and two wooden chairs positioned around a small, circular coffee table. Natural light filters through large windows, illuminating light-colored walls and warm wooden flooring.
Home in Milford
4.99 out of 5 average rating, 162 reviews

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

Top guest favourite
A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.
Cottage in Weston
4.97 out of 5 average rating, 204 reviews

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

Guest favourite
A welcoming living area features a comfortable couch and a textured ottoman, complemented by natural wood accents on the ceiling. Light fills the space from multiple windows, highlighting the hardwood floors and decorative stone wall that adds character to the room.
Cottage in Milford
4.94 out of 5 average rating, 378 reviews

Spring Sale! CozyCottage/Pet-friendly/WalktoBeach

Inspired by my Dad's wanderlust and love of sea & sand. Relax and unwind in this completely remodeled, stylish Cottage a block and a half from Long Island Sound and .9 mile to Walnut Beach - walk to coffee, pizza, lobster shack! We offer a modern kitchen, breakfast nook, dining area, natural stone wall, parking and W/D. Located in a charming coastal town - enjoy quiet neighborhood walks, coastal trails, boardwalk, breweries and restaurants. 15 min to Yale/New Haven, 65 mi to NYC.

Guest favourite
A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.
Cabin in Sherman
4.96 out of 5 average rating, 429 reviews

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..

Top guest favourite
The bedroom features a queen size spindle bed with quality bedding, flanked by two nightstands with lamps. A dedicated work desk is equipped with a lamp and USB ports. Shelving adds storage, while a small seating area is present, illuminated by natural light from the windows.
Flat in Fairfield
4.98 out of 5 average rating, 166 reviews

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.

Guest favourite
A private hot tub is situated beneath a covered patio, surrounded by blooming azaleas. The inclined garden path leads to a charming wooden house featuring a slate roof, with warm sunlight illuminating the scene. Outdoor seating is available nearby.
Home in Stratford
4.95 out of 5 average rating, 213 reviews

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.

Top guest favourite
Home in Fairfield
4.96 out of 5 average rating, 200 reviews

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.

Top guest favourite
Home in Trumbull
5 out of 5 average rating, 10 reviews

Bright & Cozy Suite with patio

Welcome to your cozy home base in Trumbull, CT! This charming guest suite offers everything you need for a comfortable and convenient stay. You'll have a private entrance and a private patio. Whether you're sipping your morning coffee or unwinding after a day of exploring, it’s a lovely spot to relax. Located in a quiet residential neighborhood, the suite is just minutes from local parks, shops and restaurants.

Superhost
A spacious living room is characterized by cathedral ceilings and large windows that frame a serene outdoor view. A contemporary sofa is complemented by unique seating and a geometric coffee table. Greenery and curated decor enrich the warm ambiance of the space.
Home in Shelton
4.84 out of 5 average rating, 104 reviews

Mid-Century Modern House - Ciela Haus

IG: @cielahaus A mid-century modern home with cathedral ceilings, carefully curated interiors and a warming indoor charcoal BBQ. It is the perfect getaway for a group of friends or family to explore the outdoors, farms, wineries or to simply enjoy tranquility. I hope you enjoy staying here as much as I loved renovating, curating and styling it!

Popular amenities for Trumbull holiday rentals

When is the best time to visit Trumbull?

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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 house rentals with a dedicated workspace in Trumbull?

    Yes! Work meets play with ease at over 20 house rentals in Trumbull featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Are there family-friendly house rentals in Trumbull?

    Trumbull has more than 10 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Are there pet-friendly house rentals in Trumbull?

    Four-legged friends are welcome in Trumbull. Choose from more than 10 house rentals for guests traveling with pets.

  • Do house rentals in Trumbull have air conditioning?

    Absolutely! We offer over 30 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 € 35 per night before taxes and fees

  • Verified guest reviews

    Over 940 verified reviews to help you choose

  • Family-friendly holiday rentals

    10 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    40 of Trumbull holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill and Laptop-friendly workspace across Trumbull rentals

  • 4.7 Average rating

    Trumbull stays receive an average rating of 4.7 out of 5 from guests