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Cruise Vacations - Vacation Rentals in Old Saybrook

Cozy Yacht with Marina Views From US $219
         

8.8 (8 Reviews)
Boat Rental
Cozy Yacht with Marina Views
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety

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Luxury Places to Stay in Old Saybrook

Over 483+ Luxury Places to Stay in or Near Old Saybrook
Stunning Seascape Home For A Dream Family Holiday From US $2,875
         

10.0 (1 Review)
Cottage
Stunning Seascape Home For A Dream Family Holiday
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront Estate Home - Beach and Shared Pool - West From US $1,978
         

9.8 (7 Reviews)
House
Waterfront Estate Home - Beach and Shared Pool - West
  • Air Conditioner
  • Parking
  • Pool

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Hollow Brook Estate From US $1,726
         

10.0 (2 Reviews)
House
Hollow Brook Estate
  • Air Conditioner
  • Balcony/Terrace
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Paradise in Clinton! AIR-CONDITIONED From US $1,507
         

9.8 (6 Reviews)
House
Paradise in Clinton! AIR-CONDITIONED
  • Air Conditioner
  • Parking
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River Front Home Good for Family and Groups From US $1,395
         

New
House
River Front Home Good for Family and Groups
  • Air Conditioner
  • Parking
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Stunning Ocean view with Hot tub. Sleeps 10 From US $1,323
         

10.0 (5 Reviews)
House
Stunning Ocean view with Hot tub. Sleeps 10
  • Air Conditioner
  • Parking
  • TV

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Beachfront Cottage with panoramic views of Long Island Sound in Madison CT From US $1,323
         

10.0 (4 Reviews)
Cottage
Beachfront Cottage with panoramic views of Long Island Sound in Madison CT
  • Air Conditioner
  • Parking
  • Pet Friendly

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Fall Colors surround our Victorian Mansion on Bashan Lake CT Amazing Views From US $1,285
         

9.8 (17 Reviews)
House
Fall Colors surround our Victorian Mansion on Bashan Lake CT Amazing Views
  • Air Conditioner
  • Parking
  • Pool

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Top-Rated Vacation Rentals with a Pool in Old Saybrook

Over 52+ Top-Rated Vacation Rentals with a Pool in or Near Old Saybrook
New Madison beach house - Ocean front- Great views- booking Summer 2025 From US $806
         

10.0 (68 Reviews)
House
New Madison beach house - Ocean front- Great views- booking Summer 2025
  • Air Conditioner
  • Parking
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Marina Guest House From US $189
         

10.0 (53 Reviews)
House
Marina Guest House
  • Air Conditioner
  • Parking
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Spacious 5-bedroom, 6 bath vacation home just 30 min drive to beaches and casino From US $1,083
         

10.0 (46 Reviews)
House
Spacious 5-bedroom, 6 bath vacation home just 30 min drive to beaches and casino
  • Air Conditioner
  • Parking
  • Pool

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Waterfront oasis 4 bdr house in Old Saybrook direct waterfront amazing sunsets From US $556
         

10.0 (7 Reviews)
House
Waterfront oasis 4 bdr house in Old Saybrook direct waterfront amazing sunsets
  • Air Conditioner
  • Parking
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Victorian beach house and cottage family compound with large pool in Westbrook From US $1,216
         

10.0 (5 Reviews)
House
Victorian beach house and cottage family compound with large pool in Westbrook
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  • Parking
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Beachfront home with heated pool From US $1,173
         

10.0 (2 Reviews)
House
Beachfront home with heated pool
  • Air Conditioner
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Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6 From US $545
         

10.0 (1 Review)
House
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
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Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6 From US $545
         

10.0 (1 Review)
Resort
Water's Edge Resort and spa w indoor and outdoor pool and beach. Condo Sleeps 6
  • Air Conditioner
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  • Pool

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Pet-Friendly Vacation Rentals in Old Saybrook

Over 142+ Pet-Friendly Vacation Rentals in or Near Old Saybrook
Spacious yard and view of Long Island Sound- walk to secluded beach! From US $465
         

10.0 (63 Reviews)
House
Spacious yard and view of Long Island Sound- walk to secluded beach!
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  • Parking
  • Pet Friendly

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The Homestead From US $331
         

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9.8 (99 Reviews)
Bed & Breakfast
The Homestead
  • Air Conditioner
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Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy From US $172
         

9.6 (83 Reviews)
Cabin
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
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You and your Family deserve a break. Relax and enjoy lake front living From US $476
         

10.0 (52 Reviews)
House
You and your Family deserve a break. Relax and enjoy lake front living
  • Air Conditioner
  • Parking
  • Pet Friendly

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Stunning Waterfront Home with Private Beach! From US $520
         

10.0 (50 Reviews)
House
Stunning Waterfront Home with Private Beach!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Beach House steps to private beaches in sought after location! From US $496
         

10.0 (46 Reviews)
House
Beach House steps to private beaches in sought after location!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Stunning Artisan Waterfall Escape [Walk to Downtown] From US $342
         

10.0 (44 Reviews)
House
Stunning Artisan Waterfall Escape [Walk to Downtown]
  • Air Conditioner
  • Parking
  • Pet Friendly

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Great family home, fenced in back yard and Weber grill. From US $454
         

10.0 (37 Reviews)
House
Great family home, fenced in back yard and Weber grill.
  • Air Conditioner
  • Parking
  • Pet Friendly

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Large Vacation Homes & Villas in Old Saybrook

Over 67+ Large Vacation Homes & Villas in or Near Old Saybrook
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included From US $868
         

10.0 (34 Reviews)
House
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
  • Air Conditioner
  • Parking
  • Pet Friendly

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Saybrook Manor Beach House From US $285
         

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8.0 (1 Review)
House
Saybrook Manor Beach House
  • Air Conditioner
  • Parking
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PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/4 QUEENS 2 FULL From US $804
         

10.0 (29 Reviews)
House
PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON W/4 QUEENS 2 FULL
  • Air Conditioner
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  • Pet Friendly

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Beach duplex—2 full homes with private access, backyard, and ocean views! From US $861
         

10.0 (24 Reviews)
Cottage
Beach duplex—2 full homes with private access, backyard, and ocean views!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Remote private, w/5 acre pond and w/Shooting Range @ Devils Hopyard State Park From US $782
         

10.0 (10 Reviews)
House
Remote private, w/5 acre pond and w/Shooting Range @ Devils Hopyard State Park
  • Air Conditioner
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  • Pet Friendly

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4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill From US $867
         

9.8 (79 Reviews)
Cottage
4BR Beach Cottage sits on private beach. Sleeps 12 with comfort, Outdoor grill
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront Estate Home - Beach and Shared Pool - East From US $1,087
         

9.8 (46 Reviews)
House
Waterfront Estate Home - Beach and Shared Pool - East
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  • Parking
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Charming beach home, complete with pool & cozy guest house! From US $855
         

9.8 (38 Reviews)
House
Charming beach home, complete with pool & cozy guest house!
  • Air Conditioner
  • Parking
  • Pool

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Wheelchair Accessible Vacation Homes in Old Saybrook

Over 14+ Wheelchair Accessible Vacation Homes in or Near Old Saybrook
Available July 21-28, 2023 From US $334
         

8.8 (3 Reviews)
Resort
Available July 21-28, 2023
  • Air Conditioner
  • Parking
  • Pool

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Water's Edge Resort & Spa From US $189
         

|
8.7 (404 Reviews)
Resort
Water's Edge Resort & Spa
  • Air Conditioner
  • Parking
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Saybrook Point Resort & Marina From US $352
         

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9.6 (1002 Reviews)
Hotel
Saybrook Point Resort & Marina
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  • Parking
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Perfect getaway to relax and experience country living in an elegant East Cost. From US $450
         

New
Other
Perfect getaway to relax and experience country living in an elegant East Cost.
  • Air Conditioner
  • Pool
  • TV

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Saybrook Point Resort & Marina From US $278
         

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9.2 (316 Reviews)
Hotel
Saybrook Point Resort & Marina
  • Air Conditioner
  • Parking
  • Pet Friendly

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Madison Beach Hotel From US $282
         

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9.4 (338 Reviews)
Hotel
Madison Beach Hotel
  • Air Conditioner
  • Parking
  • TV

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The Griswold Inn From US $255
         

8.6 (254 Reviews)
Hotel
The Griswold Inn
  • Air Conditioner
  • Parking
  • TV

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Water's Edge Resort & Spa From US $202
         

|
8.8 (1008 Reviews)
Resort
Water's Edge Resort & Spa
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Old Saybrook Varoom and Airbnb Places to Stay Under $200

Over 52+ Old Saybrook Varoom and Airbnb Places to Stay Under $200
Cozy cottage near downtown Clinton, Marina & Hammonasset Park From US $197
         

10.0 (83 Reviews)
Cottage
Cozy cottage near downtown Clinton, Marina & Hammonasset Park
  • Air Conditioner
  • Parking
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Higganum House B&B From US $158
         

10.0 (1 Review)
Bed & Breakfast
Higganum House B&B
  • Air Conditioner
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The Captain Stannard From US $178
         

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9.8 (257 Reviews)
Bed & Breakfast
The Captain Stannard
  • Air Conditioner
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Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown From US $158
         

10.0 (27 Reviews)
Apartment
Cozy Comforts! Country living at its finest - just 10 min to downtown Middletown
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Year Round Beach house From US $188
         

10.0 (20 Reviews)
House
Year Round Beach house
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1-bedroom cottage with Grove Beach 🏖️ access. From US $167
         

9.2 (36 Reviews)
Cottage
1-bedroom cottage with Grove Beach 🏖️ access.
  • Air Conditioner
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Walk to Beach, pool, tennis court and kids playscape. From US $169
         

New
House
Walk to Beach, pool, tennis court and kids playscape.
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Cozy 3-bedroom cottage in charming Westbrook with AC, private backyard patio
New
From US $118
         

New
Cottage
Cozy 3-bedroom cottage in charming Westbrook with AC, private backyard patio
  • Air Conditioner
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  • TV

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Instantly Bookable Vacation Homes in Old Saybrook

Over 200+ Instantly Bookable Vacation Homes in or Near Old Saybrook
The Perfect Family Beachfront Cottage The Viola Cottage From US $456
         

10.0 (34 Reviews)
Cottage
The Perfect Family Beachfront Cottage The Viola Cottage
  • Air Conditioner
  • Parking
  • TV

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1860's Colonial House Near Downtown and Beaches! From US $749
         

10.0 (11 Reviews)
House
1860's Colonial House Near Downtown and Beaches!
  • Air Conditioner
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  • Pet Friendly

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Remodeled 4 BR Waterfront Beach House with all the Comforts of Home.and more! From US $488
         

9.8 (20 Reviews)
House
Remodeled 4 BR Waterfront Beach House with all the Comforts of Home.and more!
  • Air Conditioner
  • Parking
  • TV

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Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage From US $456
         

9.8 (26 Reviews)
Cottage
Newly Remodeled 2 Bedroom Cottage On The Beach. The Kaitlyn Cottage
  • Air Conditioner
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Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook From US $220
         

10.0 (66 Reviews)
Cottage
Summer Cottage with Water Views at Great Hammock Beach in Old Saybrook
  • Air Conditioner
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Relaxing summer rental, walking distance to the beach, short ride to the outlets From US $411
         

9.8 (48 Reviews)
House
Relaxing summer rental, walking distance to the beach, short ride to the outlets
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Now with TV - Relax in our 3-bedroom Westbrook cottage at West Beach From US $297
         

9.6 (4 Reviews)
Cottage
Now with TV - Relax in our 3-bedroom Westbrook cottage at West Beach
  • Air Conditioner
  • Parking
  • TV

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Direct waterfront renovated cottage. From US $692
         

10.0 (84 Reviews)
Cottage
Direct waterfront renovated cottage.
  • Air Conditioner
  • Parking
  • TV

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About Old Saybrook Vacation Rentals

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Cruisevacations Old Saybrook, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Old Saybrook. Places to stay near Old Saybrook with prices averaging $219 a night.

Cruisevacations makes it easy and safe to find and compare vacation rentals in Old Saybrook with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Old Saybrook

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Use these Quick Filters to Find a Vacation Rental in Old Saybrook

★ Pro Tip: Cruisevacations makes it easy to compare the best listings on Cruisevacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Cruisevacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Old Saybrook.

Weather in Old Saybrook

View the weather forecast for Old Saybrook before booking your Old Saybrook Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Old Saybrook, CT

Cruisevacations offers a large selection of top attractions around Old Saybrook. Research things to do on your vacation before you visit Old Saybrook.


Essex Steam Train Hammonasset Beach State Park Essex Library Clinton Crossing Premium Outlets Goodspeed Opera House Tanger Outlets Harvey's Beach Devil's Hopyard State Park Ivoryton Playhouse Essex Saybrook Antique Village Shopping Center Gillette Castle State Park Anna Mia's Cockaponset State Forest Katharine Hepburn Cultural Arts Center Crystal Lake Town Park Millers Pond State Park Clinton Plaza Shopping Center Museum of Fife and Drum Banner Country Club Meigs Point Nature Center

Other Places to Stay Near Old Saybrook, CT


Middlesex County 350 Properties Saybrook Manor 214 Properties Madison Center 85 Properties Westbrook Center 80 Properties Westbrook 80 Properties East Haddam 68 Properties Deep River Center 63 Properties Clinton 60 Properties Haddam 53 Properties Old Saybrook Center 45 Properties Madison 43 Properties Killingworth 38 Properties

Complexes around Old Saybrook, CT


Water Edge Resort Beach 7 Properties Econo Lodge Inn Suites Saybrook 3 Properties Quality Inn Saybrook 3 Properties Beach Town 2 Properties Madison Beach Sound 2 Properties Scranton Seahorse Inn 2 Properties Water Edge Resort 2 Properties Beach Cottage 1 Properties Cornfield Point Cottage 1 Properties