rocks at low tide on beach at Harkness State Park

Old Saybrook Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
3 Jul - 5 Jul
In two months
14 Aug - 16 Aug
In three months
11 Sept - 13 Sept
In four months
9 Oct - 11 Oct

Our top choices for Old Saybrook holiday rentals

1 bedroom, desk, iron/ironing board, travel cot

1-bedroom cottage with Grove Beach 🏖️ access.

1-bedroom cottage with Grove Beach 🏖️ access.
Clinton
9.6 out of 10, Exceptional, (45 reviews)
"The place was super cozy and the host was wonderful! "
United States
Philip L.
The price is HK$1,051
HK$1,951 total
includes taxes & fees
28 Jun - 29 Jun
1-bedroom cottage with Grove Beach 🏖️ access.
Private kitchen

Charming 2-bedroom house with WiFi, AC in lovely Waterford

Charming 2-bedroom house with WiFi, AC in lovely Waterford
Waterford
10.0 out of 10, Exceptional, (1 review)
"The home was very clean and welcoming."
United States
Michelle M.
The price is HK$1,724
HK$3,598 total
includes taxes & fees
17 Jun - 18 Jun
Charming 2-bedroom house with WiFi, AC in lovely Waterford
Exterior

Cozy Lakefront Tiny House

Cozy Lakefront Tiny House
East Lyme
10.0 out of 10, Exceptional, (4 reviews)
"gorgeous tiny home on a tranquil lake!"
United States
Richard R.
The price is HK$1,034
HK$2,092 total
includes taxes & fees
17 Jun - 18 Jun
Cozy Lakefront Tiny House
Beach nearby

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
The price is HK$949
HK$2,509 total
includes taxes & fees
17 Jun - 18 Jun
Private 2nd-Floor Apt | 4 Mins to Beach | EV Charger & Parking Included
1 bedroom, free WiFi, bed sheets

Lakefront Boho Tiny House

Lakefront Boho Tiny House
East Lyme
10.0 out of 10, Exceptional, (5 reviews)
"Every thing was amazing "
United States
Annaliaa C.
Lakefront Boho Tiny House
Interior

Adorable Cottage, 5 min walk to water & town

Adorable Cottage, 5 min walk to water & town
Westbrook Center
9.4 out of 10, Exceptional, (15 reviews)
"Very nice small place to stay by the beach and close to great coffee shop. "
United States
Donovan V.
The price is HK$1,397
HK$3,287 total
includes taxes & fees
17 Jun - 18 Jun
Adorable Cottage, 5 min walk to water & town
Exterior

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Old Saybrook Center
9.6 out of 10, Exceptional, (47 reviews)
"Lovely cottage! Enjoyed our stay! "
United States
Joyce S.
The price is HK$3,526
HK$6,080 total
includes taxes & fees
21 Jun - 22 Jun
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds
Interior

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, (138 reviews)
"Yvette was so communicative and made the stay great! The house was amazing and everything was cozy and comfortable. It was great for a group!"
United States
Hayley T.
The price is HK$3,095
HK$6,027 total
includes taxes & fees
22 Jun - 23 Jun
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
Beach nearby

adorable ranch in beach community

adorable ranch in beach community
Old Saybrook
10.0 out of 10, Exceptional, (45 reviews)
"The experience was a pleasure - the house is comfy, and the location amazing! "
United States
Matthew V.
The price is HK$3,917
HK$6,522 total
includes taxes & fees
15 Jul - 16 Jul
adorable ranch in beach community
Beach

Beachside Bliss w/ Game Room, Gym & Golf Green

Beachside Bliss w/ Game Room, Gym & Golf Green
Westbrook
10.0 out of 10, Exceptional, (1 review)
"Perfect house for 6 guests. Loved that it was close to the beach."
United States
Shannon G.
The price is HK$2,801
HK$6,153 total
includes taxes & fees
1 Jul - 2 Jul
Beachside Bliss w/ Game Room, Gym & Golf Green
Outdoor dining

Direct Lakefront - Stunning Views and Panoramic Sunsets

Direct Lakefront - Stunning Views and Panoramic Sunsets
East Lyme
10.0 out of 10, Exceptional, (1 review)
"Very peaceful and quiet. Beautiful view of the lake. Would definitely book again."
United States
James C.
Direct Lakefront - Stunning Views and Panoramic Sunsets
Dining

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, (38 reviews)
"Enjoyed our stay"
United States
Nicole L.
The price is HK$9,403
HK$14,167 total
includes taxes & fees
3 Jul - 4 Jul
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Beach nearby

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

1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
Westbrook Center
The price is HK$1,999
HK$4,247 total
includes taxes & fees
7 Jul - 8 Jul
1st Floor Westbrook Anchor | 2 Queen Beds | EV Charger | Near Beach
1 bedroom, bed sheets

Safari Tent Glamping,S4-CedarPt, East Hampton, NY

Safari Tent Glamping,S4-CedarPt, East Hampton, NY
East Hampton
The price is HK$1,684
HK$2,550 total
includes taxes & fees
28 Jun - 29 Jun
Safari Tent Glamping,S4-CedarPt, East Hampton, NY
Terrace/patio

Cliffside Resort Condominiums

Cliffside Resort Condominiums
3.0 star property
Greenport
9.0 out of 10, Wonderful, (256 reviews)
"Beautiful property- we would definitely stay there again"
United States
Allison
The price is HK$1,754
HK$2,344 total
includes taxes & fees
23 Jun - 24 Jun
Cliffside Resort Condominiums
Smart TV

The Horse Carriage 2 miles from Foxwoods Casino

The Horse Carriage 2 miles from Foxwoods Casino
Preston
10.0 out of 10, Exceptional, (4 reviews)
"Super short stay but welcoming, clean and convenient for location"
United States
Christina S.
The price is HK$2,100
HK$4,236 total
includes taxes & fees
1 Jul - 2 Jul
The Horse Carriage 2 miles from Foxwoods Casino
View from property

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
2.0 star property
East Haddam
9.6 out of 10, Exceptional, (156 reviews)
"Great stay! "
United States
Tanitra
The price is HK$1,128
HK$1,658 total
includes taxes & fees
16 Jul - 17 Jul
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Flat-screen TV

North Fork Resort

North Fork Resort
3.0 star property
Greenport
9.2 out of 10, Wonderful, (23 reviews)
"Great stay & great staff!"
United States
James
The price is HK$2,990
HK$3,416 total
includes taxes & fees
30 Jun - 1 Jul
North Fork Resort
Exterior

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village

Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Stonington
9.8 out of 10, Exceptional, (180 reviews)
"A bright and cozy vibe as well as being thoroughly equipped with everything to make our stay comfortable.We appreciated the winter escape and enjoyed Stonington, Mystic, and Westerly. A lovely stay!"
United States
Dawn R.
The price is HK$979
HK$2,270 total
includes taxes & fees
18 Jun - 19 Jun
Comfortable Living in Casual 100 yr old Home, 10 min walk to Stonington Village
Smart TV

The Tiny Cottage on The Pond

The Tiny Cottage on The Pond
Oakdale,
10.0 out of 10, Exceptional, (9 reviews)
"I'll stay again if in the area. "
United States
Jeffrey H.
The price is HK$881
HK$1,170 total
includes taxes & fees
21 Jun - 22 Jun
The Tiny Cottage on The Pond
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.
View all properties
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

Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

10/10 Excellent
"Clean room and pleasant staff. Very quiet stay. We would book again in the near future. The parking was a little tight on a Friday night."
Myrna 3-night trip
Posted 2 hours ago
Best Western Executive Hotel Of New Haven - West Haven

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:

  • View our selection of featured holiday rentals in Old Saybrook
  • Use the map to find apartments and other holiday homes in the Old Saybrook neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Old Saybrook while they last

Look no further and take a look at our great range of rental properties in Old Saybrook!

Frequently asked questions

Can I find a holiday rental in Old Saybrook?

Yes, there are holiday rentals in Old Saybrook close to Katharine Hepburn Cultural Arts Center, or you can select a more secluded 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 holiday rentals that Old Saybrook has to offer?

Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly: This highly rated holiday home rental in Old Saybrook is located near the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

How many holiday rentals will I find in Old Saybrook?

Choose from 51 Expedia holiday rentals in Old Saybrook for a memorable holiday.

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

Family-friendly attractions include Stay and Play LLC and Saybrook Country Barn, 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 General William Hart House.

What’s a holiday rental in Old Saybrook like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Old Saybrook. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.