
Beachfront holiday rentals in Old Saybrook
Find and book unique beachfront homes on Airbnb
Top-rated beachfront rentals in Old Saybrook
Guests agree: these beachfront homes are highly rated for location, cleanliness and more.

Niantic River Beach Cottage | Waterviews
Kick back and relax in this quiet, stylish New England beach cottage with water views, a private neighborhood beach, an outdoor shower, and a sunny patio for coffee or evening wine. Just minutes from downtown Niantic, you’ll find beaches, cafés, bakeries, ice-cream stands, seafood, boutiques, boat launches, trails, outdoor concerts, and more—all within a short drive or bike ride. Perfect for a romantic getaway, a family weekend, or some quiet coastal downtime. See why guests love staying here!

“The Lighthouse” A Beach Cottage by the Sea!
Relax at this unique and tranquil getaway. Long Island Sound to the left, hiking trails to the right. Come kick your feet up at this quiet dead-end road. Enjoy all the modern amenities in this gem of a cottage community. Restaurants and nightlife are just a quick stroll away. Avoid roadside hotels and take a vacation for a night, week, or longer! Check in anytime and at your convenience!No keys to lose or to return! This property provides secure, keyless entry with an August Smart Lock!

Vinola-Lakeside Cabin on Beach Pond with Sauna
Vinola is the "Cabin in the Woods" you've been looking for! Enjoy an idyllic escape from the city year-round. Activities include swimming, fishing, hiking, kayaking or just a cozy snooze with a book on the couch. Top off your stay by trying our traditional wood-fired Finnish sauna. Relax tired muscles and rejuvenate the soul. Private beach and lake access on Beach Pond just 335 feet from the cabin. Check our photos and reviews! Our guests consistently remark that one night isn't enough.

Cozy Home In Short Beach Community
A cozy home in a beach community that has a central location with easy access to outdoor activities & local restaurants. The home is also 5 minutes from the Branford Train Station, Stony Creek Brewery, & Branford's town center. We are also a 10 minute drive from New Haven, home to Yale University, Yale Hospital and other colleges/universities. Our guests also gain access to Johnsons' Beach, a private residents only beach, located just around the corner from the home(4min walk/900ft)

Updated cottage "Beriozka" on Cedar Lake
Originally from Russia (hence the name “Beriozka” meaning Birch Tree) I live in Stamford CT. About 7-8 years ago I’ve discovered Chester/ Essex area and fell in love. I’ve been coming here during summer to enjoy river rides, during winter just to see snow on the ground of old towns and needless to say during fall – when all the beauty of nature unfolds. Then came an idea to have an own place here and when an opportunity came to buy this small cottage on Cedar Lake I’ve jumped on it.

Waterfront Joshua Cove Cottage with private beach.
Beautiful architecturally designed 1 Bedroom + loft Cottage on Joshua Cove in Guilford. The sunsets are spectacular from your own private beach. Enjoy Fall Foliage, swimming, fishing, and some of the best Kayaking from this perfect setting. Minutes from the Guilford train station, restaurants, shopping, and historic town green. The property is just 15 minutes from New Haven, and the Yale campus. The Thimble Island cruise, and the Ct. river steam train/cruise are nearby as well.

PRIVATE BEACH: A SLICE OF HEAVEN @ NIANTIC
INSTANT BOOK: Oct 2025 - Jan 2027 All Dates Open Availability ALL SUMMER '2026: June + July + Aug Available to Instant Book Steps away from CT Shoreline in back of beach house Amazing Views - Waterfront Outdoor Seating (2nd week May - until Nov 6th) *certain holidays/summer excluded in booking minimums *discounts applied to nightly rate only *we can not combine multiple discounts, yet highest % will apply *if available, also apply 10% non-refundable booking option

Coastline View Studio
This sun drenched studio apartment is perfect for families, couples or friends looking to get away and discover Montauk! Located in Montauk's harbor district. This unit is perfectly located to experience all that Montauk has to offer... Sit back on the balcony and enjoy a glass of wine as the sun sets perfectly over Culloden Point. A short walk to the Harbor, the Dock, Gosmans, TTs, Salivars, Sunday Funday, La Fin, Viking Fleet (fishing, Whale watching & Ferry).

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..

The Blue Heron at Amston Lake
3 BEDROOM Quiet Cottage: ~3 minute walk to the Main Beach at private Amston Lake. ~ Fully stocked open floor plan kitchen. Dining table seats 4 with additional seating on covered patio accessible by sliding door. ~Gas grill ~Large, private backyard with fire pit and hammock. ~Canoe and kayak available ~Adult bicycles (2) available upon request. ~Ping pong table, dart board in basement. ~ Close to Airline Trails, vineyards, breweries, casinos, and parks.

Greenport Beach house Mini Resort Spa & Catering
Nestled steps from the beach, and all that Greenport and the North Fork has to offer, this exquisitely charming 3 bedroom 2 bathroom waterfront home is absolutely delightful.. You’ll love my place because of the views, the location, the people, the ambiance, the outdoors space, and the Saltwater pool.. My place is good for couples, solo adventurers, business travelers, families (with kids), groups, and furry friends (pets).

Coastal New England Waterfront Home-The Reed House
The Reed House – Waterfront Getaway in Waterford, CT Enjoy the best of both relaxation and adventure at The Reed House, located in the peaceful Pleasure Beach neighborhood of Waterford. This charming home offers breathtaking views of Jordan Cove and is just steps away from the beach, making it the ideal retreat for families, friends, or anyone looking to unwind by the water..
Popular amenities for beachfront rentals in Old Saybrook
Pet-friendly beachfront home rentals

Walk-To-The-Beach House In The Dunes

Charming 2BR Beach House, Overlooking the Water

Pet-Friendly Private Beach Oceanfront Cottage A/C

Milford Beach House - Newer Construction!

Breezy Waterfront Home With private Dock

Charming Waterfront cottage

Charming Fairfield Beach 3BR Cottage By The Sea

Hamptons WaterLiving-Dock, Kayak, Beach, EV charge
Beachfront home rentals with a pool

Endless Summer Studio Condo w Balcony Bayview

Beautiful Waterview Condo on the North Fork of LI

Coastal Escape w/ Pool - Near Niantic & Beaches

Montauk 4bd/3.5ba Ocean, pool spa & private beach.

North Fork Sound Front Home with Pool

Waterfront Autumn Escape in Wine Country: 2BR

Beachside Waterview 2Br Condo w/ Pool in Greenport

Waterfront Condo C-204 at The Cliffside Resort
Private beachfront home rentals

Historic East Hampton Home - Private Beach Access

Adults Only Toes In The Sand Beachfront Charmer

Soundscape Beachfront House!

Charming Madison, CT Carriage House ocean rental

Oceanfront Getaway - Quiet, Firepit + Pvt Beach

Kayaks ~ Bikes ~ Boards ~ 6mins> Greenport ~ 55"TV

Niantic Cove Waterfront Escape: Relax & Unwind

Spacious Waterfront Getaway
Quick stats about beachfront rentals in Old Saybrook

Total holiday rentals
Explore 10 holiday rentals in Old Saybrook

Nightly prices starting at
Old Saybrook holiday rentals start at ₹17,567 per night before taxes and fees

Verified guest reviews
Over 530 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

Wifi availability
10 of Old Saybrook holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Old Saybrook rentals

4.9 Average rating
Old Saybrook stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Plainview Holiday rentals
- New York City Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Mount Pocono Holiday rentals
- The Hamptons Holiday rentals
- Rentals with outdoor seating Old Saybrook
- Cottage rentals Old Saybrook
- Rentals with a patio Old Saybrook
- Rentals with beach access Old Saybrook
- House rentals Old Saybrook
- Pet-friendly rentals Old Saybrook
- Beach house rentals Old Saybrook
- Waterfront rentals Old Saybrook
- Family-friendly rentals Old Saybrook
- Rentals with a firepit Old Saybrook
- Rentals with a fireplace Old Saybrook
- Rentals with a washing machine and dryer Old Saybrook
- Beachfront rentals Connecticut
- Beachfront rentals United States
- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Fairfield Beach
- Southampton Beach
- Cooper's Beach, Southampton
- Point Judith Country Club
- Ocean Beach Park
- Walnut Public Beach
- Shinnecock Hills Golf Club
- Blue Shutters Beach
- Groton Long Point Main Beach
- Napeague Beach
- Cedar Beach
- TPC River Highlands
- Brownstone Adventure Sports Park
- Silver Sands Beach
- Woodmont Beach
- Jennings Beach
- Sandy Beach
- Wildemere Beach
- Ninigret Beach
- Seaside Beach
- Outer Beach at Smith Point County Park