Search Cottages in Old Saybrook

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct
Sweet Cottage in Beach Community
Cozy kitchen with a dining area, featuring a window with a view of bare trees, a coffee maker, and a toaster.

Sweet Cottage in Beach Community

10.0 out of 10, Exceptional, (10)
"Cute cottage, newly refurbished, quiet, nice neighborhood, well stocked."
Sweet Cottage in Beach Community
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
Enjoy a serene beachside escape with access to the ocean.

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

9.8 out of 10, Exceptional, (92)
"This is a great place to stay in Greenport. It has a private beach and is quiet and friendly. It's a 2-minute drive to town and shops, but you will want to spend your time enjoying the beautiful waterfront views."
'The Gate House'on Beach front Estate with Dockage. Walk to Village .
A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington
Cozy attic retreat with a bunk bed, bedside table, and dormer window.

A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington

10.0 out of 10, Exceptional, (1)
"We visited here for a weekend in the Mystic area. Our daughter joined us for an evening and the home was cozy and comfortable for 3 adults. The check in process was seamless and communication with the host was always timely. They thought of everything to make our stay enjoyable and everything was within arms reach. The home is located in a great spot and enabled us to enjoy many surrounding areas. Pawcatuck/Westerly, Mystic, Watch Hill... all were very close so this was a perfect base of...
The price is HK$1,570
HK$3,046 total
includes taxes & fees
2 Sept - 3 Sept
A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington
Lakeside cottage overhanging the water, beautiful window views across the lake
Enjoy a serene lake view from the comfort of your room, which features a deck with a table and chairs.

Lakeside cottage overhanging the water, beautiful window views across the lake

9.8 out of 10, Exceptional, (206)
"Great cottage right on the water! Cute swings on the deck! The hot tub was great! "
The price is HK$2,661
HK$4,457 total
includes taxes & fees
27 Aug - 28 Aug
Lakeside cottage overhanging the water, beautiful window views across the lake
Go Jump in the Lake!
Explore serene lakeside tranquility with a variety of canoes available for use.

Go Jump in the Lake!

10.0 out of 10, Exceptional, (141)
"Spent Christmas at the cottage with my family and we had an amazing time!! I highly recommend! Beautiful place, beautiful area! The host was fantastic and very responsive! 10/10! "
Go Jump in the Lake!
Direct waterfront renovated cottage.
Relax in this airy living room with a sofa, chest of drawers, and wicker chair, offering a view of the sea.

Direct waterfront renovated cottage.

10.0 out of 10, Exceptional, (76)
"Perfect stay in Madison. Beautiful location. Clean and comfy house. Will be back!"
Direct waterfront renovated cottage.
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Relax in comfort with a table and four chairs, perfect for enjoying refreshments and conversation.

4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill

9.8 out of 10, Exceptional, (72)
"We stayed at this property last year and again this year. You can’t beat the location and the house is perfect for a group of family or friends. We had a lovely time and look forward to another stay in the future!"
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
Cozy Home near private beach , close to New Haven area colleges Hospitals
Relax in this serene outdoor seating area with a bird-patterned cushion and a vase of fresh flowers.

Cozy Home near private beach , close to New Haven area colleges Hospitals

9.6 out of 10, Exceptional, (64)
"Joel was terrific, very responsive. The “cozy cottage” was everything we were expecting and hoping for. We plan to return."
Cozy Home near private beach , close to New Haven area colleges Hospitals
Lovely Cottage in the Heart of Long Island Wine country
Enjoy a serene beach experience with calm seas and sandy shores.

Lovely Cottage in the Heart of Long Island Wine country

9.8 out of 10, Exceptional, (26)
"Our family stayed at this quaint cottage in the North Fork. The cottage has a nice kitchen, gas fireplace, and well appointed bedrooms. I would love to visit in summer, it must be wonderful!"
Lovely Cottage in the Heart of Long Island Wine country
Charming 3-bedroom cottage short walk to Chalker Beach
Relax in a comfortable seating area with a sofa and armchairs, perfect for unwinding in front of the large flat-screen TV.

Charming 3-bedroom cottage short walk to Chalker Beach

10.0 out of 10, Exceptional, (2)
"Lovely location very close to Harvey's Beach and local attractions . Home is very well kept in a quiet neighborhood "
Charming 3-bedroom cottage short walk to Chalker Beach
Spacious 2BR Norwich Cottage
Relax on the deck surrounded by trees and a serene body of water.

Spacious 2BR Norwich Cottage

9.6 out of 10, Exceptional, (19)
"We had a great time. Our new puppy loved walking the grounds (on leash inside and out). Very private and close to all we wanted to see...seaport, restaurants, casinos. Loved our stay there. Thanks for everything."
Spacious 2BR Norwich Cottage
Historic Whitneyville Cottage
Compact kitchen with a stainless steel refrigerator, double sink, and oven, complete with white cabinetry and a countertop.

Historic Whitneyville Cottage

9.4 out of 10, Exceptional, (16)
"My wife and I, and our little dog, had a great experience staying at the Yellow Cottage. For our needs, it was perfectly located. It's on a busy street, but the traffic noises wound down at night. Much nicer than the hotels in the area."
Historic Whitneyville Cottage
Lakeside cottage ON the water with beautiful views up the lake!
Relax on the dock with a serene lakeside view, perfect for a peaceful retreat.

Lakeside cottage ON the water with beautiful views up the lake!

9.8 out of 10, Exceptional, (182)
"Enjoyable and comfortable, great spot to chill."
The price is HK$3,053
HK$4,964 total
includes taxes & fees
31 Aug - 1 Sept
Lakeside cottage ON the water with beautiful views up the lake!
Charming Westbrook Cottage, Steps to Private Beach
Enjoy cooking in this well-equipped kitchen with an oven, microwave, and refrigerator.

Charming Westbrook Cottage, Steps to Private Beach

9.8 out of 10, Exceptional, (6)
"Had a great stay!"
Charming Westbrook Cottage, Steps to Private Beach
DIRECT WATERFRONT PRIVATE BEACH
Guests can enjoy the beach and calm sea from the comfort of their accommodations.

DIRECT WATERFRONT PRIVATE BEACH

9.4 out of 10, Exceptional, (23)
"This rental was perfect. Super clean and comfy with the most amazing views. Loved that it’s right on the water with a private beach. We will definitely book this property again."
DIRECT WATERFRONT PRIVATE BEACH
Private Guest House w/ Deck + Spectacular Views!
Escape to a serene cabin nestled among lush greenery, surrounded by trees and shrubs.

Private Guest House w/ Deck + Spectacular Views!

10.0 out of 10, Exceptional, (32)
"We were in town for a volleyball tournament for our daughter and had an amazing stay. It was so easy. Al is a wonderful proprietor. The refrigerator is stocked with basics so you don't have to bring everything. The setting is stunning and the pool was fun :) Highly recommend!"
Private Guest House w/ Deck + Spectacular Views!
1-bedroom cottage with Grove Beach 🏖️ access.
Relax in comfort with a sofa, throw blanket, and natural light pouring in through the large window.

1-bedroom cottage with Grove Beach 🏖️ access.

9.2 out of 10, Wonderful, (28)
"Loved the overall stay and experience. The private beach access is a bonus"
The price is HK$1,053
HK$2,019 total
includes taxes & fees
1 Sept - 2 Sept
1-bedroom cottage with Grove Beach 🏖️ access.
Privately Located Beach Cottage Getaway
Enjoy a relaxing day at the beach with access to safety measures and comfortable seating.

Privately Located Beach Cottage Getaway

9.6 out of 10, Exceptional, (50)
"Quaint and close to beach, shopping and restaurants"
Privately Located Beach Cottage Getaway
Beach Pass included. Tidy, quiet house w/ Porch. Sleeps 7
Traditional two-story house with a gabled roof and chimney, set amidst a well-manicured lawn and lush gardens.

Beach Pass included. Tidy, quiet house w/ Porch. Sleeps 7

9.6 out of 10, Exceptional, (86)
"Wonderful stay!"
Beach Pass included. Tidy, quiet house w/ Porch. Sleeps 7
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Enjoy cooking in this well-equipped kitchen with a central island, oven, and microwave.

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

9.6 out of 10, Exceptional, (37)
"We had such a nice stay, the house was clean and had everything we needed."
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Old Saybrook Hotel Reviews

Quality Inn Old Saybrook - Westbrook

Quality Inn Old Saybrook - Westbrook

10/10 Excellent
"Nice place to rest."
Kenneth 1-night trip
Posted 12 hours ago
Quality Inn Old Saybrook - Westbrook

Frequently asked questions

How much do cottages in Old Saybrook cost?
Expect to pay between HK$1,053 and HK$3,053 per night for cottages in Old Saybrook. No matter your budget, a terrific stay is only clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Old Saybrook?
Claim your holiday time and pick from 236 cottages in Old Saybrook. Yearning for a place where you can get in touch with nature? Expedia will help you find your ideal stay in only a click or two.
Why book your cottage in Old Saybrook with Expedia?
Expedia has some terrific cottages in Old Saybrook, so start planning for an unforgettable holiday on nature's doorstep. If you have a fixed budget, click on how much you're willing to spend and your preferred property star rating. Or, use our filters to search for cottages with a pool or free WiFi. We'll help you find the perfect pad whatever your getaway looks like.