
Places to stay near Anchor Beach
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Top-rated vacation rentals near Anchor Beach
Guests agree: these stays are highly rated for location, cleanliness, and more.

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!

Spacious 4 bedroom, oasis with ocean views galore
Scio by the sound is a home that is steps from the water, overlooking the Long Island Sound. Whether you want to lounge by the in ground pool or walk to the beach, you will find your happy place here. The home sleeps up to eleven guests in beautiful Milford, CT with a great location to local beaches and downtown Milford. It is also the perfect place with a large private backyard great for families for vacations or a friends get together or for a local wedding. The possibilities are endless!

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!

Bright 1 BR Apt Steps From Yale
Enjoy a bright and cozy 1 bedroom apartment just 2 blocks from the Yale campus and The Shops at Yale. Located in a 3 unit brick building, designated as a property on The National Register of Historic Places, this small renovated 2nd floor apartment maintains the characteristics of the building's original design, while providing all amenities needed for a comfortable stay. Convenient free off street parking provided. Great shops, restaurants, nightlife, and museums can all be accessed by foot.

Fall Sale! Cozy Bungalow/Walk2Beach/Pet-friendly
Welcome to the Beach Bungalow, completely remodeled to the studs in '21! This Woodmont by the Sea home is a 3 block stroll to Anchor Beach & the walkway along beautiful Beach Ave. The home offers a modern kitchen, dining for 6, private back porch & outdoor shower. This +775sf bungalow has a driveway & on-street pkg. It's located in a charming coastal town, walking distance to restaurants, grocery store & Robert Treat Farm and is 2 mi to I95, 10 mi to Yale/New Haven...and mins to breweries.

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.

Cozy Milford Beach House
Charming beach house in lovely New England neighborhood. Walking distance to a few small little restaurants/bars and small shopping plaza. Beautiful hard wood floors throughout with carpets to make a warm inviting home. An updated on-demand hot water heater as well as a brand new washing machine updated 2021. Porch has a lovely ocean view with enough seating to eat outside or just hang out with a nice glass of vino or coffee. A few minutes from downtown Milford, train station and Gulf Beach.

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.

King 1BR Apt with Cozy Den and Luxury Amenities
This gorgeous apt, located in a brand-new luxury building at the center of New Haven’s historic downtown, offers unparalleled comfort, service, and amenities. You can watch a movie on a 65" HDTV, work in one of 5 co-working spaces, or relax at the pool w/ grills and cabanas. Highlights: • Walkable access to Yale • Deep-clean prior to every guest • Coffee, fresh linens, and bathroom essentials • 24/7 fitness center • Rooftop sun terrace + grills • Entertainment lounge w/ bowling alley

Retreat in New Haven by Stephanie and Damian
Welcome to your retreat in the heart of Westville. This apartment features a spa-like bathroom and a cozy living room with a super-comfy couch and large flatscreen TV. Relax in this centrally located oasis near Yale’s football stadium, Westville Bowl, local art studios, coffee shops, and top restaurants just steps away. Perfect for extended stays, traveling professionals, visiting faculty, or anyone seeking a convenient home base this winter. Discounts for stays of 30+ days.

A Beachfront Getaway
Welcome to your dream beachfront escape! This delightful 1-bedroom beach house cottage is your ticket to an unforgettable coastal retreat. Nestled on the picturesque West Shore, this cozy cottage offers everything you need for a relaxing getaway, just steps away from the sun, sand, and surf. Situated in the heart of the West Shore, our beachfront cottage boasts a convenient location that puts you within easy reach of local restaurants, shops, universities and transportation.

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.
Popular amenities for vacation rentals near Anchor Beach
Condo rentals with wifi

Clean 1 BD apt with Free Wi-Fi and parking

Stunning, Spacious, Spotless. Close to Yale.

Cozy Condo by Fairfield U/SHU | Patio | Wshr/Dryr

Downtown gem w/ parking, Wi-Fi+!

Chateau Blanc Yale

1856 Trading House close to water

Brownstone Downtown New Haven | Central Yale

Sunrise Retreat: Luxe Master Suite, Ocean Views!
Family-friendly house rentals

Westshore Luxury

Jan/Feb longer stays avail! Inquire! New Firepit!

Private 1-Bdrm Apt in West Haven

Beach House steps from sand & Amazing Views

Seaside Cottage: water views, walk to beaches!

Cozy Studio in Bridgeport

Steps from the Beach with Large Private Backyard!

Charming 3 bedroom Beach Front Cottage
Apartment rentals with air conditioning

Downtown, Private balcony, 1gb fiber Wi-Fi

Renovated Apartment in a Historic Farmhouse Estate

Your CT Pizza Palace awaits! - Full Apartment

Stylish Sheek Loft Ricport Studio 2, Downtown

Cozy & Private Apartment Near the Ocean

Peaceful apartment on 3.5 acres w/ Artist studio.

Huckleberry Quarters, the Cozy Redding Retreat.

Cozy and Quiet space to Relax
Other great vacation rentals near Anchor Beach

Beautiful, Spacious, Waterfront Home on the Bay

Charming Riverview Home*Firepit* Near Train & I-95

Beach condo

Beautiful Cozy Apt/ Soaking Tub & Serene Vibes

Beachy Bay Breeze Bungalow 2BR with parking and close to many amenities.

Long Term Stay Option/ Private Suite near beach

Newly Restored Cottage on River

Beach Apartment in Woodmont Milford
Destinations to explore
- Yale University
- Fairfield Beach
- Southampton Beach
- Rye Beach
- Cooper's Beach, Southampton
- Gilgo Beach
- Robert Moses State Park
- Ocean Beach Park
- Thunder Ridge Ski Area
- Walnut Public Beach
- Shinnecock Hills Golf Club
- Bethpage State Park
- Rye Playland Beach
- TPC River Highlands
- Cedar Beach
- Brownstone Adventure Sports Park
- Woodmont Beach
- Silver Sands Beach
- Sunken Meadow State Park
- Jennings Beach
- Amagansett Beach
- Sandy Beach
- Wildemere Beach
- Kent Falls State Park




