
Cottage vacation rentals in Old Saybrook
Find and book unique cottages on Airbnb
Top-rated cottage rentals in Old Saybrook
Guests agree: these cottages are highly rated for location, cleanliness, and more.

Luxury cottage by the sea with hot tub and pool
We built this guest cottage to provide an ultimate luxury experience for people wanting to escape from hectic life!With incredible coastal views, this home is a haven of tranquility. It sits on a special stretch of the Connecticut coast, with spectacular bird and wild life-watching year-round. Enjoy great shopping in Guilford's boutiques around the historic town green. Watch the sun set over the water and relax in the hottub for some night time star gazing year round (pool open June-beg/mid Oct)

New! “LaBoDee”
“LaBoDee”, a fun play on the word abode, house, is a tiny cottage located central to CT’s unique shoreline communities, just off I95. “LaBoDee” is one room with a fully equipped kitchenette, ready for those who would like to stay awhile. “LaBoDee” is on a property contiguous to a state forest (a trail is right outside the door) yet within walking distance is a delicious deli, market, gas station, pizza, a lake, and close by is the beach. A local restaurant has day passes for their beach- $20!!

Peaceful Riverfront Cottage w/Dock, Walk to Beach
This lovely Cottage sits directly on the Patchogue River with scenic views of the river and marshlands from every room and just a 1/4 mile walk or bike to the Beach. Private, but close to so much, it’s Perfect for a Romantic Getaway, or a long Vacation. Outside, you can enjoy the breeze from the Riverfront Deck, Sun Bathe, Crab or Fish on the Lower Dock, watch the Eagles fly by, or wander about the wooded property. Bring or rent a Kayak and paddle down the river right to the Long Island Sound.

Mystic Cottage Retreat, near downtown
This recently renovated cottage is at the top of a quiet lane with a sweeping meadow view. Single level. Two bedrooms sleep four (queen and two twin beds); new, well-equipped kitchen and one bath, open living area, deck and patio. Light and spacious. Working fireplace, central A/C; W/D; expanded cable TV and wifi; off street parking for two cars. Market/deli nearby; pleasing walk (less than a mile from center of Mystic)- restaurants, shops, marinas, etc. Near Amtrak station. Great retreat!

Cozy Home In Short Beach Community
A cozy home in a beach community which is in a central location with easy access to many outdoor activities(private beach access) & local restaurants. The location is also 5 minutes from the Branford Train Station, Stony Creek Brewery, Branford's town center. New Haven the home of Yale University, Yale Hospital and other colleges in the New Haven area are a short drive The house is across the street from Farm River. across the street in opposite direction is a short walk to Johnsons beach.

Newly Built Cottage in Housatonic Valley
This newly built modern cottage is located on a historic railroad street nestled in a charming village within the Housatonic River Valley. There are beautiful river views from the front porch, deep woods off the back deck, a white marble kitchen with new appliances, and a dedicated parking spot. Escape the city and surround yourself in this quiet valley and the calm of small village life, located just 2 hours from NYC. This location offers year-round access to nature & outdoor activities.

Welcome to The Holly at Amston Lake
Welcome to The Holly at Amston Lake! Great two-bedroom cottage situated in a peaceful lake community. Great place to enjoy time with family and friends. Take a stroll down to the main beach or enjoy the great views of the lake from the deck! Don't forget about the gas fire pit for those chilly evenings. We are located near numerous vineyards, a brewery, the Connecticut Airline Trail, and great local restaurants! Guests have access to the grill, fire pit, kayaks, and two main beaches.

EASY BEAT
LOVELY MID 1800'S COTTAGE Located in the historic Groton Bank neighborhood. Close to beaches, casinos, walking distant to EB. Short drive to Pfizer, Coast Guard Academy, Connecticut College, US Submarine Base and minutes to downtown Mystic. This property is a one bedroom one bath with a single pullout couch in bedroom and living room. Offers a spacious outside lawn with patio. Lots of off street parking. Fenced yard for pets. New Central Air and heat. Washer, dryer, grill and fire pit.

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.

Beautiful View 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.

The Cottage at Indian Cove
A charming original turn of the century cottage that was recently renovated. One main room plus a full bathroom and Ikea kitchen. It includes a back porch that gets a perfect amount of late afternoon sun. The cottage has electric baseboard heat for cool nights. We are located in Indian Cove beach Association with a two block walk to the beach. You are welcome to enjoy our kayaks, bikes to tour the area and a fire pit.
Popular amenities for Old Saybrook cottage rentals
Cottage rentals with a hot tub

Magical Lakeside – Lake Zoar Views & Private

Cozy Lakefront Cottage w/Swim Spa & Firepit

Walk/Bike to East Hampton Village & Ocean Beaches

Litchfield-Hot Tub-Shops & Eats-Vineyards-Hikes

4 Br Beach House; Short Walk to Beach!

Lakefront Escape | Hot Tub + Cozy Fall Retreat

Cozy Getaway | Pet Friendly | Litchfield Cty

Lakefront Cottage Complete with Kayaks!
Pet-friendly cottage rentals

Foxfire Hill: A Bit of Luxury in the Countryside

Private and Serene home close to I-84 and shopping

In-law apartment in Farmington River Cottage

SILVER SANDS BEACH COTTAGE MILFORD NEAR YALE/TRAIN

Cozy Cottage by the pond

Cozy Country Cottage #3

Stuart Cottage/Minutes to Mohawk Ski Area

Lakefront Cozy Oasis 2BR w/ stunning sunset views
Private cottage rentals

Peaceful Oceanfront Cottage

The Snug Cottage: Walk to Water-Newly Renovated

Vintage Bolton Lake

Go Jump in the Lake!

The Carriage House Skiing Nearby

Luxury Driftwood Cottage @ Saybrook Point

Guest House at the Marina

Serene Coastal Cottage steps from South Cove
Quick stats about cottage rentals in Old Saybrook
Total vacation rentals
Explore 20 vacation rentals in Old Saybrook
Nightly prices starting at
Old Saybrook vacation rentals start at ﺩ.ﺇ294 per night before taxes and fees
Verified guest reviews
Over 770 verified reviews to help you choose
Family-friendly vacation rentals
10 properties offer extra space & kid-friendly amenities
Pet-friendly vacation rentals
Find 10 rentals that welcome pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
10 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!
Destinations to explore
- Plainview Vacation rentals
- New York Vacation rentals
- Long Island Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Philadelphia Vacation rentals
- South Jersey Vacation rentals
- Mount Pocono Vacation rentals
- The Hamptons Vacation rentals
- Rentals with a fire pit Old Saybrook
- Rentals with outdoor seating Old Saybrook
- Rentals with a fireplace Old Saybrook
- House rentals Old Saybrook
- Rentals with a patio Old Saybrook
- Pet-friendly rentals Old Saybrook
- Family-friendly rentals Old Saybrook
- Beach house rentals Old Saybrook
- Waterfront rentals Old Saybrook
- Rentals with beach access Old Saybrook
- Rentals with a washer and dryer Old Saybrook
- Beachfront rentals Old Saybrook
- Cottage rentals Connecticut
- Cottage 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