
Waterfront vacation rentals in Old Saybrook
Find and book unique waterfront rentals on Airbnb
Quick stats about waterfront rentals in Old Saybrook

Total vacation rentals
Explore 30 vacation rentals in Old Saybrook

Nightly prices starting at
Old Saybrook vacation rentals start at G$27,189 GYD per night before taxes and fees

Verified guest reviews
Over 1,090 verified reviews to help you choose

Family-friendly vacation rentals
30 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Old Saybrook vacation rentals include wi-fi 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!
Top-rated waterfront rentals in Old Saybrook
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

Beachfront Paradise
Beautiful beachfront home available weekly in season third week of June through Labor Day) and nightly (2 night min.) off season. Step out the door and into the sand. Sit on the porch and watch sailboat races from Niantic Bay Yacht Club just steps away. Close to downtown Niantic with restaurants, shops, etc. 18 miles from Mohegan Sun Casino. Attractions within 1/2 hour: Beautiful Mystic, CT, several vineyards, Harkness State Park, Eugene O'Neill Theatre, U.S. Coast Guard Academy, golf courses.

Spacious Oceanfront Getaway with Spectacular Views
Perfect vacation getaway! Awaken to the sun rising over Long Island Sound! Panoramic waterfront views from 70 ft of windows spanning NY to RI. Quiet, private, updated home, NOT a cottage: >2200 sq ft, single level 3B/3B, + bonus lower-level walk-out/office. Master bed double shower/jacuzzi overlooking the water! Multiple oceanfront decks. 100 ft granite shoreline, short stroll to nearby sand beaches. Swim, fish, read a book, or watch the sailboats go by! (Not suitable for children/pets/events.)

True Ocean Front Vacationing - Groton/Mystic
Bright and airy contemporary beach house with breathtaking views of Long Island Sound. Conveniently located just 15 mins to Mystic/Stonington; 23 to Foxwoods/Mohegan Sun . Relax on the lower deck and drop a fishing line in the ocean as it greets the seawall at high tide. Or retreat to a private roof deck to enjoy your favorite beverage as you take in the most romantic time of the day, the golden hour featuring beautiful sunsets. Parking for 3-4 cars. We hope you enjoy this escape by the sea!

Romantic Getaway at The Lake!
Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

A Beach House Gem
Beautiful beach cottage with a private beach. Sleeps up to 6 comfortably with two full beds and 1 queen in the master. with a beautiful balcony Full bath upstairs,1/2 off the kitchen entrance outside key on the key chain The main living area has a TV, air conditioning, and sliding doors to a deck. The updated kitchen has a dishwasher, microwave, cooktop, oven, and coffee maker. There are 2 parking spots in front of the garage The house is not winterized there are no bookings from Nov1

Thames River Retreat · CT College+Casinos+USCGA
This home on the Thames River is the ultimate getaway for a family seeking relaxation and outdoor adventures. With five bedrooms, three and a half bathrooms, a spacious kitchen, and a comfortable living room with stunning views of the water and private beach. The master bedroom with on suite bathroom, large deck overlooking the river, with direct access to the backyard where you can lounge on the private beach, play lawn games, or take a dip in the river. We have 2 kayaks available for use.

Beautiful lakefront retreat just 15 mins to casino
Beautiful waterfront home with unobstructed views of Oxoboxo Lake! Quiet area yet just 30 minutes to Mystic. Upper level has 2 cozy bedrooms – one with a queen bed and one with 2 twin beds, a spacious living area with direct lake views, and a full bathroom. Lower level has a second mini kitchen with fridge, sink, microwave and table, large living room, bathroom, and doors leading directly onto the lakeside patio. Lower level has a twin size bed in living area for extra sleeping space.

Steps to Beach • Hot Tub • Game Room • Water Views
Beautiful coastal beach house directly across from a private beach and tennis club with complimentary guest access. Backing up to a serene marsh with stunning views, this home offers a peaceful, upscale setting perfect for families and groups. Relax in the hot tub with outdoor TV, fire pit, and kayaks. Inside features 4 bedrooms, a workspace, and a new game room with a 100” TV, pool table, shuffleboard, and darts. Minutes from Branford’s town center, dining, and waterfront attractions.

Salty Breeze - Waterfront Cottage on the Cove
Enjoy your stay in this peaceful waterfront cottage. After the day relax on the 3 season screened- in porch or climate controlled sunroom watching the winter waterfowl on the wintery cove or relax in the backyard next to the fire pit with hot coco. Walking distance to Ocean Beach Park, Waterford Town Beach. Within 30 minutes of Niantic, downtown Mystic, Ferry's to Block, Fisher's and Long Islands, by museums, the Nautilus, Mohegan and Foxwoods Casinos, tons of great restaurants

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.

Amazing 2BR Riverfront Gem
Unwind at this happy getaway on the river. Extremely comfortable house with amazing views in a peaceful neighborhood. The well-equipped kitchen overlooking the river is a pleasure for any cook. You will love to see our fairy-lit lawn, wishing well, chimenea, and charming décor. Only minutes to beaches, groceries, coffee shops, hiking trails and amazing CT scenery at every turn! Other favorites include Chamard Vineyard, Shopping Outlets, fantastic Restaurants, music, and lots more.

Belle Vue Cottage
Welcome to "Belle Vue Cottage". This charming and inviting cottage is located in a quiet and peaceful neighborhood in the South Cove area of Old Saybrook. Spend your days relaxing at Harvey's Beach, perusing the shops and restaurants along Main Street, taking in a show at The Kate, and unwind at the end of the day in your backyard oasis equipped with an outdoor TV and fire pit. We are less than a mile from Saybrook Point Inn and Spa, and 10 minutes to Water's Edge Resort and Spa.
Popular amenities for Old Saybrook waterfront rentals
Waterfront apartment rentals

"Meteor": River View Penthouse in Downtown Mystic

Mystical Ocean View in Historic Stonington Borough

The Millhouse Downtown Chester

Large Waterfront Luxury Apartment

Coastal Relaxation Getaway

Beautiful studio overlooking the Mystic River

Water front studio apartment with fireplace.

Lovely Waterfront Apartment in Gales Ferry CT
Waterfront house rentals

Lake House w/Game Rm 5 Min From Foxwoods & Mohegan

Estate with lake near beaches & Westerly

Hot tub with river & casino view

Lake Home w/Game Room 5 Min To Foxwoods & Mohegan

Luxe Bolton Lake

Red Bird Waterfront Home. Dock available extra!

Waterfront Oasis 4Bdr/2b

Addison’s Oasis
Waterfront condo rentals

Beautiful condo on Long Islands Northfork

Waterfront Escape | Private Beach, Pool & Views

Beautiful Waterview Condo on the North Fork of LI

King Bed - hot tub - saunas - 1 mile Mohegan Sun

Coastline View Studio

Montauk Waterfront Condo w/ Sunset Views

Beautiful Condo on the Ocean Bluffs

The Bridge at Soundview · Beach+OceanView+Sunrise
When is the best time to visit Old Saybrook?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$54,169 GYD | G$65,254 GYD | G$65,254 GYD | G$78,639 GYD | G$86,587 GYD | G$95,371 GYD | G$94,116 GYD | G$90,979 GYD | G$83,659 GYD | G$67,973 GYD | G$60,234 GYD | G$62,744 GYD |
| 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 |
Destinations to explore
- New York Vacation rentals
- Montreal Vacation rentals
- Philadelphia Vacation rentals
- Washington Vacation rentals
- Boston Vacation rentals
- Ocean City Vacation rentals
- Jersey City Vacation rentals
- Portland Vacation rentals
- Newark Vacation rentals
- Baltimore Vacation rentals
- Atlantic City Vacation rentals
- Newport Vacation rentals
- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- Cooper's Beach, Southampton
- East Matunuck State Beach
- Fairfield Beach
- Ocean Beach Park
- Charlestown Beach
- Mystic Seaport Museum
- Mystic Aquarium
- Southampton Beach
- University of Connecticut
- University of Rhode Island
- Soundview Beach
- Powder Ridge Mountain Park & Resort
- Hammonasset Beach State Park
- Wölffer Estate Vineyard
- Ocean Beach
- Sleeping Giant State Park
- Ski Sundown
- Orient Beach State Park
- Meschutt Beach
- Ditch Plains Beach
- Wesleyan University





