A rocky beach with large boulders and the ocean in the background.

Old Saybrook Vacation Rentals

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Old Saybrook vacation rentals

Interior

1. Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats

Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Saybrook Manor
9.8 out of 10, Exceptional, (140 reviews)
"This house comfortably sleeps a lot of guests and has a well equipped kitchen. Everything was very clean. The hosts were very easy to communicate with and very helpful."
United States
Alexis L.
The price is ￥45,181
￥85,295 total
includes taxes & fees
Sep 28 - Sep 29
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Interior

2. Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.2 out of 10, Wonderful, (17 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is ￥25,979
￥73,983 total
includes taxes & fees
Sep 22 - Sep 23
Adorable Cottage, 5 min walk to water & town
Dining

3. Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Old Saybrook
9.8 out of 10, Exceptional, (41 reviews)
"Enjoyed our stay"
United States
Nicole L.
The price is ￥86,284
￥146,134 total
includes taxes & fees
Sep 24 - Sep 25
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Beach nearby

4. 1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Great spot Very clean"
United States
Dorothy W.
The price is ￥28,711
￥70,028 total
includes taxes & fees
Sep 22 - Sep 23
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Beach

5. Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (2 reviews)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is ￥37,792
￥99,978 total
includes taxes & fees
Sep 23 - Sep 24
Beachside Bliss w/ Game Room, Gym & Golf Green
1 bedroom, desk, iron/ironing board, travel crib

6. 1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (60 reviews)
"We enjoyed our stay"
United States
JM B.
The price is ￥19,061
￥36,173 total
includes taxes & fees
Oct 20 - Oct 21
1-bedroom cottage with Grove Beach 🏖️ access.
Coffee/tea maker, fridge, microwave, oven

7. The gardners Cottage 1 mile from long Island Sound - pet friendly

The gardners Cottage 1 mile from long Island Sound - pet friendly
Clinton
9.8 out of 10, Exceptional, (28 reviews)
"Enjoyed our stay - Highly recommend!"
United States
Mary S.
The price is ￥27,454
￥48,711 total
includes taxes & fees
Oct 7 - Oct 8
The gardners Cottage 1 mile from long Island Sound - pet friendly
Exterior

8. Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (5 reviews)
"gorgeous tiny home on a tranquil lake!"
United States
Richard R.
The price is ￥22,261
￥45,666 total
includes taxes & fees
Sep 24 - Sep 25
Cozy Lakefront Tiny House
Outdoor dining

9. Direct Lakefront - Stunning Views and Panoramic Sunsets

Direct Lakefront - Stunning Views and Panoramic Sunsets
East Lyme
10.0 out of 10, Exceptional, (2 reviews)
"We really enjoyed our stay. It was very peaceful and relaxing. The view of the lake from sunrise to sunset was truly breathtaking."
United States
Chuck T.
The price is ￥34,341
￥70,610 total
includes taxes & fees
Sep 24 - Sep 25
Direct Lakefront - Stunning Views and Panoramic Sunsets
TV, books

10. Direct waterfront renovated cottage.

Direct waterfront renovated cottage.
Madison Center
10.0 out of 10, Exceptional, (96 reviews)
"Great cottage on the Sound!"
United States
David S.
The price is ￥109,816
￥174,960 total
includes taxes & fees
Sep 28 - Sep 29
Direct waterfront renovated cottage.
1 bedroom, WiFi (free), bed sheets

11. Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (10 reviews)
"Every thing was amazing "
United States
Annaliaa C.
The price is ￥21,226
￥44,319 total
includes taxes & fees
Sep 23 - Sep 24
Lakefront Boho Tiny House
Beach nearby

12. Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included

Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Westbrook Center
10.0 out of 10, Exceptional, (1 review)
"Able to walk to all the nearby restaurants with this location, including the beach. Very clean rooms with 2 TVs and controllable AC. Would definitely visit here again."
United States
Mason T.
The price is ￥20,421
￥50,139 total
includes taxes & fees
Sep 22 - Sep 23
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
Sun loungers, beach towels

13. Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!

Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Madison
10.0 out of 10, Exceptional, (2 reviews)
"Cozy cottage was perfect for our long weekend in Madison!"
United States
Samantha D.
The price is ￥22,873
￥54,346 total
includes taxes & fees
Oct 6 - Oct 7
Welcoming 1-Bedroom Cottage in Charming Madison is One Mile to Town and Beach!
Desk, laptop workspace, bed sheets

14. Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.5 star property
East Haddam
9.4 out of 10, Exceptional, (191 reviews)
"Beautiful cabin! Will def go again!"
United States
Morainny
The price is ￥20,238
￥30,490 total
includes taxes & fees
Sep 22 - Sep 23
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Flat-screen TV

15. North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.6 out of 10, Exceptional, (56 reviews)
"Friendly staff. Clean room had everything we needed. Enjoyed our stay!"
United States
Harold
The price is ￥44,405
￥50,733 total
includes taxes & fees
Oct 18 - Oct 19
North Fork Resort
Condo | Terrace/patio

16. Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (292 reviews)
"Great place!"
United States
Christine
The price is ￥43,192
￥66,752 total
includes taxes & fees
Oct 5 - Oct 6
Cliffside Resort Condominiums
Beach nearby

17. Forecastle at Soundview · Beach+OceanView+Sunrise

Forecastle at Soundview · Beach+OceanView+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (1 review)
"The location is perfect, just a few houses from the beach. The unit has a great view, very clean and new. The owners/managers were very prompt and communicative. I was VERY hesitant to book a place without reviews- but this was an excellent choice. The beach is clean and private, people are friendly. I will happily stay again!"
United States
megan g.
The price is ￥24,261
￥46,183 total
includes taxes & fees
Sep 22 - Sep 23
Forecastle at Soundview · Beach+OceanView+Sunrise
Beach nearby

18. Keel at Soundview · Beach+OceanView+Sunrise

Keel at Soundview · Beach+OceanView+Sunrise
Old Lyme
10.0 out of 10, Exceptional, (3 reviews)
"Very peaceful community. Great accommodations!"
United States
Joseph O.
The price is ￥20,824
￥41,620 total
includes taxes & fees
Sep 22 - Sep 23
Keel at Soundview · Beach+OceanView+Sunrise
Outdoor dining

19. Lakeside Bliss

Lakeside Bliss
East Lyme
9.6 out of 10, Exceptional, (31 reviews)
"Lovely house - excellently equipped and fun decor. The owner was gracious and flexible and the location is beautiful. "
United States
Brenda M.
The price is ￥56,336
￥86,084 total
includes taxes & fees
Sep 27 - Sep 28
Lakeside Bliss
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

Best Western Mystic Hotel

Best Western Mystic Hotel

8/10 Good
"Room was very clean, staff were very helpful, polite and attentive. All room appliances worked. The breakfast was not very good. Not much variety and everything was very plain."
Melinda 2-night trip
Posted 8 hours ago
Best Western Mystic Hotel

Find out more about Old Saybrook

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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 Katharine Hepburn Cultural Arts Center, 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?

Steps to the Beach, Cozy Year Round Cottage Pet Friendly: Visitors like this Old Saybrook vacation home rental. It is located near the beach and has a patio, a garden, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. Make the most of the selection of games in this rental home to help you unwind.

How many vacation rentals will I find in Old Saybrook?

Choose from 46 Expedia vacation rentals in Old Saybrook for a memorable vacation.

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

Harvey's Beach and Connecticut River are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Saybrook Country Barn. 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.