
House holiday rentals in Old Saybrook
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Top-rated house rentals in Old Saybrook
Guests agree: these houses are highly rated for location, cleanliness and more.

Niantic River Beach Cottage | Waterviews
Kick back and relax in this quiet, stylish New England beach cottage with water views, a private neighborhood beach, an outdoor shower, and a sunny patio for coffee or evening wine. Just minutes from downtown Niantic, you’ll find beaches, cafés, bakeries, ice-cream stands, seafood, boutiques, boat launches, trails, outdoor concerts, and more—all within a short drive or bike ride. Perfect for a romantic getaway, a family weekend, or some quiet coastal downtime. See why guests love staying here!

Year Round Beach House in Old Saybrook, CT.- Pets
Our Beautiful Home is Located in Saybrook Manor Association and only a short walk to the beach . We have 4 Bedrooms that can accomadate 8 people,pull out couch,2 bathrooms, a Dining Room,Kitchen, and Spacious Living room.Our Yard is fenced in for your privacy & pets.Our home comes with many ammenities such as movies,games,kayaks, Clamming &Crabbing tools,Bikes,Floats & Beach Chairs.We have a beautiful backyard to enjoy games,barbecue or just to relax & unwind.Enjoy our beautiful & quaint beach

Romantic Getaway at The Lake!
Beautiful year round getaway! Relax and have a glass of wine by the lake. Wake early to enjoy the sun rising directly over the lake with a fresh cup of coffee. Enjoy direct lake access on a trophy bass lake including a beautiful dock. Hot tub overlooking the water open year round. Enjoy dinner in front of beautiful gas fireplace. Amazing sunrises and colorful sunsets. The location and amenities make for a fantastic romantic getaway for two! Centrally located 30 minutes from the Mohegan Casino.

The Dragon Fly Garden
The phrase "nestled in nature” is the best way to describe the dragonfly's den. Sitting on the trail head to over 1,000 acres of the Cocaponsette State Forest across from Messerschmidt pond and just three miles from the winding salt water marsh water way you won't find a better mix of activities. Golf & boating are just moments away. Mountain biking & Trail running off the property. This country cottage boasts lake views, wildlife and wandering trails to loose yourself within. 1GB internet

Modern farmhouse w/ pool, beach, horses and winery
A new, modernized farmhouse with a heated saltwater pool in the heart of North Fork. Nestled on an acre of lush, fully fenced yard, the home can easily accommodate up to 8 guests and all pets! Minutes away from Love Lane (Mattituck's charming downtown), Breakwater Beach (one of best beaches in North Fork), Mattituck train station and surrounding the award winning Bridge Lane Vineyards and picturesque Seabrook Horse Farm, this bucolic home offers the perfect setting for a North Fork getaway.

Walk to the beach at Black Point, Niantic, Ct
Black Point beach home (5th house from water) within walking distance of three beaches. Open floor plan with three levels. Ping Pong room on lower level. Living room, dining room, sitting area, and kitchen on mid level. Three bedrooms & 2 full bath on top level. WI-Fi, linens, coffee, water provided. Fenced in back yard with gas grill. Close to casinos, charter fishing, Essex steam train, Mystic Aquarium & Seaport, and Newport (1 Hr). Walk Niantic Bay Boardwalk or Old Black Point.

Beachfront Paradise
Beautiful beachfront home available weekly in season (6/20/26-9/5/26) and nightly (2 night min.) off season. Step out the door and into the sand. Sit on the porch and watch sailboat races from Niantic Bay Yacht Club just steps away. Close to downtown Niantic with restaurants, shops, movie theatre, etc. 18 miles from Mohegan Sun Casino. Attractions within 1/2 hour: Beautiful Mystic, CT, several vineyards, Harkness State Park, Eugene O'Neill Theatre, U.S. Coast Guard Academy, golf courses.

Salty Breeze - Waterfront Cottage on the Cove
Enjoy your stay in this peaceful waterfront cottage. After the day relax on the 3 season screened- in porch or climate controlled sunroom watching the winter waterfowl on the wintery cove or relax in the backyard next to the fire pit with hot coco. Walking distance to Ocean Beach Park, Waterford Town Beach. Within 30 minutes of Niantic, downtown Mystic, Ferry's to Block, Fisher's and Long Islands, by museums, the Nautilus, Mohegan and Foxwoods Casinos, tons of great restaurants

Cozy Comforts!
Keep it simple at this peaceful and centrally-located place. Completely open concept and fully renovated. Country living yet just minutes to downtown Middletown and Wesleyan University. Come stay at our home away from home! We are about 20-25 min from the shoreline or travel in the other direction and you’ll be in our state’s capital, Hartford. We are only about 10-15 min from Wesleyan and downtown Middletown for shopping and great restaurants! You don’t want to miss this one!

The Sandpiper
Newly renovated 2-Family Home! Located right in Greenport Village providing walking distance to all the restaurants, bars, shopping, coffee shops, and Shelter Island Ferry, Long Island Railroad (LIRR), and Hampton Jitney. My place is close to restaurants and dining, the beach, family-friendly activities, nightlife, and public transport. You’ll love my place because of Location!. My place is good for couples, solo adventurers, business travelers, families (with kids).

PRIVATE BEACH: ROYAL OCEANVIEW CASTLE @ CLINTON
INSTANT BOOK: Apr 2026 - Jan 2027 = All Open Availability SUMMER 2026: June + July + Aug Steps away from CT Shoreline in back of beach house! Amazing Views - Waterfront Outdoor Deck w/ Seating (2nd week May - until Nov 6th) *certain holidays/summer excluded in booking minimums *discounts applied to nightly rate only *we can not combine multiple discounts, yet highest % will apply *if available, also apply 10% non-refundable booking option

Best of both worlds!
Great location- 1 mile to the beach, 1/2 mile to shops and restaurants, and less than a 1/4 mile to a park! The house is set back from the road with a good size driveway. The inside is newly renovated and we are working to finish the yard area for the summer! The house has WiFi, large yard, and a great front porch that gets a ton of sun. We’ve made great memories there over the years and are now looking to share it with others!
Popular amenities for house rentals in Old Saybrook
House rentals with a pool

3 BR/Pool. Walk to Beach & Town!

FREE Private Indoor Heated Pool - Mystic Home

East Hampton Oasis - Pool and Hot Tub

Sag Harbor, Designer w large Pool (3 bed/2.5 bath)

Secluded Farmhouse - Studio Apartment Style Unit

Explore the Water & Woods at a Relaxing Retreat

Casino Stay & Play House w/Hot Tub, Game Room

Beauty and the Beach!
Weekly house rentals

Seas the Day at the CT Shoreline

Newly renovated CT shoreline home next to Marinas

Romantic Couples Retreat with Private Sandy Beach

Casa Swan

4 Bedrooms Modern Home with Water View & Access

Old Lyme Farmhouse

3BR Updated Cottage w/ Pool in Old Saybrook

Secret Seaside Stone Cottage
Private house rentals

Niantic Getaway Near Beach & Boardwalk

Adorable Beach House on LI Sound

Beachside Bliss w/ Game Room, Gym & Golf Green

Tinker Gardens

Barnacle Bay Beach House

Cozy Beach Home Mid NYC-Bos/Comfy Getaway all year

Stylish Retreat Waterviews

Addison's Oasis
When is the best time to visit Old Saybrook?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $382 SGD | $361 SGD | $371 SGD | $385 SGD | $434 SGD | $502 SGD | $502 SGD | $502 SGD | $443 SGD | $413 SGD | $380 SGD | $381 SGD |
| Avg. temp | 0°C | 1°C | 4°C | 10°C | 16°C | 21°C | 24°C | 24°C | 20°C | 14°C | 8°C | 3°C |
Quick stats about house rentals in Old Saybrook

Total holiday rentals
Explore 90 holiday rentals in Old Saybrook

Nightly prices starting at
Old Saybrook holiday rentals start at $127 SGD per night before taxes and fees

Verified guest reviews
Over 2,440 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 30 rentals that welcome pets

Rentals with dedicated workspaces
40 properties have a dedicated workspace

Wifi availability
80 of Old Saybrook holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Old Saybrook rentals

4.9 Average rating
Old Saybrook stays are highly rated by guests – averaging 4.9 out of 5!
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- Family-friendly rentals Old Saybrook
- Rentals with a firepit Old Saybrook
- Cottage rentals Old Saybrook
- Pet-friendly rentals Old Saybrook
- Rentals with a fireplace Old Saybrook
- Beach house rentals Old Saybrook
- Waterfront rentals Old Saybrook
- Beachfront rentals Old Saybrook
- Rentals with outdoor seating Old Saybrook
- Rentals with a patio Old Saybrook
- Rentals with a washing machine and dryer Old Saybrook
- Rentals with beach access Old Saybrook
- House rentals Connecticut
- House rentals United States
- Yale University
- Foxwoods Resort Casino
- Charlestown Beach
- Fairfield Beach
- Cooper's Beach, Southampton
- Southampton Beach
- Ocean Beach Park
- Mohegan Sun
- East Matunuck State Beach
- Long Island Aquarium
- Hammonasset Beach State Park
- Mystic Seaport Museum
- Mount Southington Ski Area
- Powder Ridge Mountain Park & Resort
- Sleeping Giant State Park
- Burlingame State Park
- Yale University Art Gallery
- Salty Brine State Beach
- Ski Sundown
- Orient Beach State Park
- East Hampton Main Beach
- Narragansett Town Beach
- Meschutt Beach
- Wölffer Estate Vineyard




