
Places to stay near Fort Trumbull Beach
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Top-rated holiday rentals near Fort Trumbull Beach
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The Boathouse, private downtown Harborside suite
The Boathouse is a detached one bedroom studio apartment situated behind our home in the heart of Historic downtown Milford. Through a private entrance you will discover a thoughtfully furnished bedroom (queen bed & pull out couch), dining room, full kitchen & bath. It is ideally suited for a couple/small family looking for a memorable beachtown getaway. Walk, rent bikes/kayaks, shop, dine, enjoy art, music, or a day at the beach… our quintessential New England seaside town is sure to charm you!

Jan/Feb longer stays avail! Inquire! New Firepit!
*Jan and Feb available for longer stays!Inquire!* *Brand New Major Renovation in 2023* • Fully renovated, designer beach house • Steps away from quaint downtown •1 block from water •Walk to beach, restaurants, coffee, ice cream, deli & convenience store, liquor and more... • Luxe, white, 100% cotton sheets & fluffy duvets •FULLY FENCED backyard with outdoor seating, BBQ grill, & fire pit .Easy drive to Sacred Heart, Fairfield, & Yale .STEPS to Tyde wedding venue .Fiber internet for fast speed

Private Inn
Private(not shared) self check-in, clean, quiet, safe, and free off street parking on a cul de sac road. The suite is 600sq your own private bathroom, backyard, and number keypad for your convenience to enter/exit into the suite at will, there is high speed Wi-Fi, HD cable tv, Kcup machine, heat/ac (indoor fireplace) also a firepit outsde ,rubber track and tennis courts literally in the back yard. 5miles away from Yale/nh and 5mins to Griffen Hospital and major highways great local restaurants

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!

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.

Chic Coastal Retreat: Modern Apt Steps from Beach
Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

Lovely water front lower-level loft, free parking
This unique centrally located water front loft is located on the second Gulf Pond 1.5 miles from historic Milford center buzzing with water front restaurants and downtown shopping. This one bedroom, one bath, has a private entrance and free off street parking. Outdoor patio & grill with kitchenette, enjoy a waterfront view throughout the 400 sq ft space. Close to I-95, the Merrit Parkway, and Milford train station. Explore 17 miles of beaches in this New England town by bike, kayak, or foot.

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

Fall 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.

2BR Beach Escape Near Yale, NYC Train
Charming Milford Cottage-Your Coastal Escape-Beach, Town and NYC Train! This adorable cottage is perfect for a getaway, visiting colleges or traveling nurses. Enjoy a day on the beach (5 min walk), shopping/eating downtown or take the train into NYC (15 min walk). Start your day with a cup of coffee on the front porch rockers or cook a delicious meal in the well-equipped kitchen! Super cozy and charming...we can't wait to welcome you! Absolutely no parties permitted.

Oceanfront Retreat with Hot Tub
Escape to this luxurious 4-bedroom, 2.5-bath oceanfront home on the stunning Long Island Sound. Enjoy direct beach access, a private hot tub, and a fully equipped patio with a gas grill and dining area. Perfect for families or groups, this retreat offers breathtaking views, a full kitchen, arcade games, and modern amenities. Located minutes from restaurants and shops, it’s ideal for relaxation or adventure. Book now for a perfect blend of comfort and coastal charm.

Downtown, Private balcony, 1gb fiber Wi-Fi
Charming 2nd floor one bedroom apartment with a separate entrance located in Milford's Historic district south of the green. You'll be 0.4 miles to the Milford train station. It's only 0.3 miles to the Milford Green which features restaurants, nightlife, and the Milford Harbor. Three local breweries are within 20 minutes of driving. Enjoy 17 miles of coastline where you can swim, kayak, and paddle board. Check in time is flexible with self check in lockbox.
Popular amenities for holiday rentals near Fort Trumbull Beach
Apartment rentals with wifi

Clean 1 BD apt with Free Wi-Fi and parking

One bedroom cozy condo

Stunning, Spacious, Spotless. Close to Yale.

Setting Sun Waterfront Retreat on Hillside

Cozy Condo in Fairfield with Parking and Laundry!

Downtown gem w/ parking, Wi-Fi+!

1856 Trading House close to water

Cozy private furnished apartment
Family-friendly house rentals

Bobby's Beach Bungalow

Milford Beach Charles Isle Renovated Cottage 2BR

Cozy Winter Escape • Firepit • Near Train & I-95

Private 1-Bdrm Apt in West Haven

Cute 2 bed 1 bath beach house

Modern Beach Getaway

Cozy Studio in Bridgeport

Luxe cozy 2br/1ba Milford bungalow-walk to beach!
Apartment rentals with air conditioning

Urban Getaway

The Farmhouse Estate Apartment

Stylish Sheek Loft Ricport Studio 2, Downtown

Retreat in New Haven by Stephanie and Damian

King 1BR Apt with Cozy Den and Luxury Amenities

Peaceful apartment on 3.5 acres w/ Artist studio.

Huckleberry Quarters, the Cozy Redding Retreat.

Seaside Studio in Historic Bridgeport Brownstone
Other great holiday rentals near Fort Trumbull Beach

Modern 3 Bedroom Home with Beach Views

Cozy Sanctuary near Yale/ for Connection & Rest

The studio downtown

New build! 1 house from beach

Welcome 2026! Book this cozy New England space NOW

Spacious Gulf Beach Home

Walk to the beach

New & Modern Studio Apartment in Fairfield
Destinations to explore
- Yale University
- Jones Beach
- Fairfield Beach
- Southampton Beach
- Cooper's Beach, Southampton
- Rye Beach
- Gilgo Beach
- Robert Moses State Park
- Thunder Ridge Ski Area
- Bronx Zoo
- Walnut Public Beach
- Rowayton Community Beach
- Shinnecock Hills Golf Club
- Bethpage State Park
- Rye Playland Beach
- Cedar Beach
- TPC River Highlands
- Jones Beach State Park
- Brownstone Adventure Sports Park
- Woodmont Beach
- Silver Sands Beach
- Sunken Meadow State Park
- Jennings Beach
- Hudson Highlands State Park




