Old Saybrook Vacation Rentals

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Oct 1 - Oct 2
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Oct 10 - Oct 12

Vacation Rentals in Old Saybrook

Postcard Cabins Machimoodus
Standard Cabin, 1 Queen Bed | Exterior

Postcard Cabins Machimoodus

2.0 star property
9.6 out of 10, Exceptional, (70)
"Great stay"
The price is ￥20,561
￥29,599 total
includes taxes & fees
Oct 2 - Oct 3
Postcard Cabins Machimoodus
Cliffside Resort Condominiums
Beach nearby

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (241)
"Great view of the water and nice amenities with the beach and pool."
The price is ￥39,228
￥51,245 total
includes taxes & fees
Oct 2 - Oct 3
Cliffside Resort Condominiums
Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages
Private kitchen

Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages

10.0 out of 10, Exceptional, (2)
"Waterfront location by a marina was beautiful. The place is welcoming with a bright, cozy living area. Rooms were clean and spacious, bathrooms modern, kitchen, grill, and deck to enjoy. Had a great experience overall."
Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages
Luxury Furnished Apartments by Hyatus Downtown at Yale
Honeymoon Apartment, 3 Bedrooms, Kitchen | In-room dining

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.6 out of 10, Exceptional, (55)
"Loved our stay here. "
Luxury Furnished Apartments by Hyatus Downtown at Yale
Amazing Ocean Front 2 Story Home, Steps Away From The Water
Outdoor dining

Amazing Ocean Front 2 Story Home, Steps Away From The Water

9.8 out of 10, Exceptional, (97)
"Beautiful home with lots of room. Many bathrooms and lots of storage for your belongings. The view and beach are amazing and the location to have fun is perfect. "
Amazing Ocean Front 2 Story Home, Steps Away From The Water
The Stern at Soundview · Beach+Ocean+Sunrise
On the beach

The Stern at Soundview · Beach+Ocean+Sunrise

2.0 star property
10.0 out of 10, Exceptional, (3)
"I had a great experience staying at The Stern! I enjoyed celebrating my weekend there! "
The price is ￥8,389
￥25,324 total
includes taxes & fees
Oct 13 - Oct 14
The Stern at Soundview · Beach+Ocean+Sunrise
Lakeside cottage overhanging the water, beautiful window views across the lake
Outdoor dining

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

9.8 out of 10, Exceptional, (209)
"Nice home and location, included amenities very nice. "
The price is ￥29,436
￥57,223 total
includes taxes & fees
Oct 14 - Oct 15
Lakeside cottage overhanging the water, beautiful window views across the lake
Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath
1 bedroom, WiFi, bed sheets

Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath

10.0 out of 10, Exceptional, (6)
"William was great. Room was perfectly clean. Fresh towels, water bottles, croissants, and coffee everyday was a really nice touch. "
The price is ￥13,017
￥17,928 total
includes taxes & fees
Oct 12 - Oct 13
Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath
Charming houseboat in pleasant New London with AC, WiFi
Interior

Charming houseboat in pleasant New London with AC, WiFi

9.6 out of 10, Exceptional, (12)
"Very nice people. Boat was roomy and well stocked but dirty. Toilet pump was broken and made loud noises all night. We were not informed this was an issue til checkout. Some other small issues "
The price is ￥22,188
￥47,852 total
includes taxes & fees
Oct 31 - Nov 1
Charming houseboat in pleasant New London with AC, WiFi
Lakeside cottage ON the water with beautiful views up the lake!
Property grounds

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

9.8 out of 10, Exceptional, (186)
"every was very easy process and a pleasure to stay there"
The price is ￥29,436
￥57,223 total
includes taxes & fees
Oct 27 - Oct 28
Lakeside cottage ON the water with beautiful views up the lake!
Rustic Lakeside Cabin at White Gate Farm
Interior

Rustic Lakeside Cabin at White Gate Farm

10.0 out of 10, Exceptional, (120)
"Beautiful cabin on the lake. Will definitely stay again. Easy check-in easy check out. You wont regret staying here!"
Rustic Lakeside Cabin at White Gate Farm
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
Terrace/patio

Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!

10.0 out of 10, Exceptional, (13)
"Such a fun, beautiful and unique stay. Would love to stay again!"
The price is ￥26,005
￥44,766 total
includes taxes & fees
Oct 2 - Oct 3
Cozy houseboat escape surrounded by breath taking views across from Rocky Neck!
A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington
2 bedrooms, iron/ironing board, free WiFi, bed sheets

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 ￥25,886
￥52,697 total
includes taxes & fees
Oct 2 - Oct 3
A Tiny Escape - Charming Eco-Friendly Retreat Awaits in Stonington
Spacious 7-bedroom house Stonington with amazing views.
Dining

Spacious 7-bedroom house Stonington with amazing views.

10.0 out of 10, Exceptional, (5)
"Absolutely wonderful property, just beautiful and well kept. Most of all, Clean!!! John was lovely. He answered any and all questions we had ranging from the moment we booked to when we were at the location during our stay. While we were there, we were already talking about booking our next stay. If you are thinking about booking this property, do it! "
Spacious 7-bedroom house Stonington with amazing views.
Charming Studio| Near Yale| Downtown New Haven
Exterior

Charming Studio| Near Yale| Downtown New Haven

9.2 out of 10, Wonderful, (5)
"A great place to stay during reunions! Prime campus-adjacent location, an easy walk to all things on campus!"
The price is ￥15,900
￥31,057 total
includes taxes & fees
Oct 6 - Oct 7
Charming Studio| Near Yale| Downtown New Haven
The Mystic Harbor House · walk downtown Mystic · train · aquarium
Dining

The Mystic Harbor House · walk downtown Mystic · train · aquarium

10.0 out of 10, Exceptional, (4)
"Great house in a fantastic location. Very clean and well supplied. We would definitely stay here again."
The price is ￥36,004
￥78,056 total
includes taxes & fees
Oct 7 - Oct 8
The Mystic Harbor House · walk downtown Mystic · train · aquarium
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Outdoor pool

Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food

10.0 out of 10, Exceptional, (103)
"Our multigenerational long weekend loved our stay. Fab manager. House so well kitted out. "
Historic Inn on a 100 Acre Organic Farm with Lake, Private Pool & Gourmet Food
Humble Beginnings
Exterior

Humble Beginnings

10.0 out of 10, Exceptional, (5)
"We loved this property.Only stayed one night, wish we could spend more time here. Well stocked kitchen, bathroom extras in case you've forgotten some essentials at home. Electric fireplace for that special atmosphere while hanging out in the living room. Super comfy mattresses. Shower with great water pressure and extra large head. Convenient access, private parking space. Board games. Books. Quiet air purifiers in each room.I could go on and on.Definitely will stay again. Adding to favorites."
The price is ￥14,112
￥19,187 total
includes taxes & fees
Oct 2 - Oct 3
Humble Beginnings
Charming Historic House in Downtown Mystic
Smart TV, video games, books, stereo

Charming Historic House in Downtown Mystic

10.0 out of 10, Exceptional, (155)
"Such a unique home in the lovely town! Much to see and do. We need a longer stay. Thank you. "
The price is ￥30,886
￥59,038 total
includes taxes & fees
Oct 9 - Oct 10
Charming Historic House in Downtown Mystic
Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in
1 bedroom, WiFi, bed sheets

Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in

9.6 out of 10, Exceptional, (12)
"William was very thorough with our check in and a pleasure to deal with"
The price is ￥13,017
￥17,928 total
includes taxes & fees
Oct 13 - Oct 14
Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in
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.
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Top Old Saybrook Hotel Reviews

New Haven Hotel

New Haven Hotel

10/10 Excellent
"Friendly staff. Nice rooms. Good location/value."
William 1-night trip
Posted 1 day ago
New Haven Hotel

Find out more about Old Saybrook

Find out more about Old Saybrook

Search for holiday rentals in Old Saybrook on Expedia! You can easily find your home rentals, villas, holiday apartments in Old Saybrook using one of the methods below:

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Frequently asked questions

Can I find a vacation rental in Old Saybrook?

Yes, there are vacation rentals in Old Saybrook close to Saybrook Country Barn, or you can go with a more remote option if you're looking for a relaxing stay. Visitors like the popular beaches and shops in Old Saybrook. Allow some time to check out the spas during your trip.

What are some of the best vacation home rentals in Old Saybrook?

Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages: This vacation home rental outside of Old Saybrook has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals will I find in Old Saybrook?

Choose from 55 Expedia vacation rentals in Old Saybrook for a memorable vacation.

What’s there to see and do in Old Saybrook?

Family-friendly attractions include Saybrook Country Barn and Stay and Play LLC, whereas Harvey's Beach and Connecticut River are a couple of great spots to enjoy the outdoors. Other places in town to visit include Katharine Hepburn Cultural Arts Center and Essex Saybrook Antique Village Shopping Center.

What’s a vacation rental in Old Saybrook like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Old Saybrook. Vacation rentals offer extras like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for family trips.