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

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Old Saybrook vacation homes

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.
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
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, (139 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 AED 1,488
AED 2,871 total
includes taxes & fees
5 Jul - 6 Jul
Authentic 1795 Historic Homestead w/ Private Grounds for Gatherings and Retreats
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, (2 reviews)
"The home was very clean and welcoming."
United States
Michelle M.
The price is AED 808
AED 1,687 total
includes taxes & fees
5 Jul - 6 Jul
Charming 2-bedroom house with WiFi, AC in lovely Waterford
Terrace/patio

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
Clinton
10.0 out of 10, Exceptional, (30 reviews)
"It was a very clean well kept property. The accommodation was very comfortable. We all truly enjoyed the house and location. "
United States
claire
The price is AED 4,771
AED 7,551 total
includes taxes & fees
31 Jul - 1 Aug
PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/ 4 QUEENS 2 FULL
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 AED 1,014
AED 2,523 total
includes taxes & fees
6 Jul - 7 Jul
Beachside Bliss w/ Game Room, Gym & Golf Green
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 AED 1,837
AED 3,087 total
includes taxes & fees
15 Jul - 16 Jul
adorable ranch in beach community
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 AED 841
AED 1,791 total
includes taxes & fees
6 Jul - 7 Jul
Adorable Cottage, 5 min walk to water & town
Terrace/patio

Thames River Retreat · CT College+Casinos+USCGA

Thames River Retreat · CT College+Casinos+USCGA
Waterford
10.0 out of 10, Exceptional, (23 reviews)
"Beautiful view of the waters and lots ofcroom to relax."
United States
Omar
The price is AED 2,177
AED 4,026 total
includes taxes & fees
6 Jul - 7 Jul
Thames River Retreat · CT College+Casinos+USCGA
Smart TV, books

Clear LI Sound waterview, Wedding pics, Yale&Beach

Clear LI Sound waterview, Wedding pics, Yale&Beach
East Shore
10.0 out of 10, Exceptional, (11 reviews)
"Great stay! Would definitely stay again! "
United States
Frankie O.
The price is AED 2,112
AED 3,653 total
includes taxes & fees
7 Jul - 8 Jul
Clear LI Sound waterview, Wedding pics, Yale&Beach
Interior

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.

New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Durham
9.8 out of 10, Exceptional, (28 reviews)
"Wonderful house in a great location."
United States
Edward S.
The price is AED 2,387
AED 3,798 total
includes taxes & fees
5 Jul - 6 Jul
New modern, luxurious home on 2.5 acres. 10 min to Powder Ridge & Middletown.
Terrace/patio

Brand new Waterfront house | Dock | Hot Tub& Kayak

Brand new Waterfront house | Dock | Hot Tub& Kayak
Fair Haven
Brand new Waterfront house | Dock | Hot Tub& Kayak
Smart TV, fireplace, video games, DVD player

Exceptional Contemporary Coastal Retreat-4 King Bedrooms Mystic Noank Groton CT

Exceptional Contemporary Coastal Retreat-4 King Bedrooms Mystic Noank Groton CT
Groton
10.0 out of 10, Exceptional, (132 reviews)
"Loved the woods next to it. The stained glass were very cool"
United States
Kate R.
The price is AED 1,157
AED 2,447 total
includes taxes & fees
5 Jul - 6 Jul
Exceptional Contemporary Coastal Retreat-4 King Bedrooms Mystic Noank Groton CT
Property grounds

Harbor View Landing Mystic CT - The Bluffs Waterfront House - Second Floor Only

Harbor View Landing Mystic CT - The Bluffs Waterfront House - Second Floor Only
West Mystic
10.0 out of 10, Exceptional, (3 reviews)
"We had a lovely experience in West Mystick at the Harbor House. The rental was lovely, clean, and contained enough of the necessary amenities. The view of the harbor was lovely. There were renters below us that had small children and at times that was very noisy. You could hear them running back and forth most of the evening. If they were playing music you could hear that as well. It was very cold during our time in Mystic so the heat was necessary. The baseboard heat was sufficient to keep...
United States
Suzanne S.
The price is AED 1,466
AED 1,895 total
includes taxes & fees
5 Jul - 6 Jul
Harbor View Landing Mystic CT - The Bluffs Waterfront House - Second Floor Only
Marina

NEW Boutique Downtown Home, Shops, Patio, Office, Pets, Walk to Dining

NEW Boutique Downtown Home, Shops, Patio, Office, Pets, Walk to Dining
Mystic River Historic District
10.0 out of 10, Exceptional, (23 reviews)
"Great house and incredible location. Very attentive hosts. Wonderful place to stay!"
United States
Philip M.
The price is AED 3,299
AED 5,452 total
includes taxes & fees
3 Aug - 4 Aug
NEW Boutique Downtown Home, Shops, Patio, Office, Pets, Walk to Dining
Fridge, microwave, oven, stovetop

Huge Home Near Beach front with Pool and Hot Tub

Huge Home Near Beach front with Pool and Hot Tub
East Shore
Huge Home Near Beach front with Pool and Hot Tub
Interior

PRIVATE BEACH: A SLICE OF HEAVEN @ NIANTIC W/ 6 QUEENS 1 FULL BED

PRIVATE BEACH: A SLICE OF HEAVEN @ NIANTIC W/ 6 QUEENS 1 FULL BED
East Lyme
9.8 out of 10, Exceptional, (34 reviews)
"Beach access was so convenient and relaxing. "
United States
Lauren R.
The price is AED 4,625
AED 7,339 total
includes taxes & fees
5 Jul - 6 Jul
PRIVATE BEACH: A SLICE OF HEAVEN @ NIANTIC W/ 6 QUEENS 1 FULL BED
Marina

Gorgeous Waterfront 2:1 - 2 houses in 1 building.

Gorgeous Waterfront 2:1 - 2 houses in 1 building.
Fair Haven
The price is AED 2,207
AED 3,449 total
includes taxes & fees
4 Aug - 5 Aug
Gorgeous Waterfront 2:1 - 2 houses in 1 building.
Private kitchen

Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.

Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
Stonington
10.0 out of 10, Exceptional, (64 reviews)
"Can’t wait to come back!"
United States
Jackie M.
The price is AED 1,488
AED 2,801 total
includes taxes & fees
3 Aug - 4 Aug
Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
Fridge, microwave, oven, stovetop

Coastal Landing Stay

Coastal Landing Stay
East Shore
The price is AED 873
AED 2,082 total
includes taxes & fees
6 Jul - 7 Jul
Coastal Landing Stay
TV, fireplace

Beautiful Bayfront Home • Heated Pool & Jacuzzi

Beautiful Bayfront Home • Heated Pool & Jacuzzi
West Haven
The price is AED 3,074
AED 4,665 total
includes taxes & fees
12 Jul - 13 Jul
Beautiful Bayfront Home • Heated Pool & Jacuzzi
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

Winnapaug Inn

Winnapaug Inn

8/10 Good
"The room was clean and the staff were friendly. If breakfast is important to you, plan on going out. It’s the only part of my stay that was disappointing."
Jennifer 3-night trip
Posted 4 hours ago
Winnapaug Inn

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