
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.

Sunrise Beach Cottage
Our newly renovated home is steps away from Cornfield Point’s many private Beaches, tennis court, boardwalk and Sandbar. With Multiple Water views, 4 private beaches, new appliances, grill, furniture, washer dryer, beds, patio, fire pit, golf, kayaking, pickle ball , tennis, playground, clubhouse, The Kate , Casino’s , 3 lighthouses, private boat ramp. We will try to accommodate your dog too. Sat - Sat 7 night stays, other by request. Sunrises, Sunsets & Sea Breezes Academic Renters 2025

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

3BR Updated Cottage w/ Pool in Old Saybrook
Welcome to Osprey Lookout! 3 bedroom, 1 full bath updated cottage located in the quintessential New England beach town of Old Saybrook, CT. With distant views of Long Island Sound from the pool deck, this single-family cottage in a private setting has everything you need to enjoy a relaxing family vacation, including an outdoor shower to rinse off after a day at the beach! Nearby: - Harvey's Beach - Connecticut Wine Trail - Essex Steam Train - Mohegan Sun & Foxwoods - Historic Mystic Seaport

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.

Steps to Beach! *Cozy Cottage* Pet Friendly
Relax and enjoy the beach life in this newly renovated charmer just steps from The Saybrook Manor Assoc private beach which is only available to Saybrook Manor Assoc members. Enjoy cooking your favorite family meals in our fully stocked kitchen or venture out to some of the best restaurants on The CT Shore with a short 5-15 min drive. Free wifi for work or entertainment , private outdoor patio dining and serenity await you. You will feel at home in our little slice of heaven on The Shore.

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.

Niantic Bay & Play House-Game room, mins to beach
Stay at the end of a quiet cul-de-sac located half a mile from downtown Niantic with several beaches located minutes from the house. The Niantic Bay & Play House is packed full of indoor and outdoor games while conveniently located close to several attractions. Sit by the fire pit, play Corn Hole or Frisbee Golf in our large open private backyard. Inside you will find big open spaces to relax with friends and family. Our house is perfect for everyone including your furry family member.

Waterside Beach Retreat
Beautiful New England period home steps from the beach on the Long Island Sound. Recently renovated from top to bottom with new kitchen and bathrooms, hardwood floors throughout. Idyllic location on quaint & quiet street. Hide away and relax or discover the many local attractions - water sports, fishing, winery, antique stores, scenic walks, premium outlet shopping are all on your doorstep. Ideally located off the I-95 halfway between NYC & Boston, both of which are a train ride away.

Red Bird Waterfront Home. Dock available extra!
Looking for a stylish and spacious place to stay for your next group trip? Look no further than this waterfront home, perfect for families looking to relax and create lasting memories by the ocean. Interested in hosting an event? Ask us! This beautiful home offers stunning views of the water and plenty of space for your family to enjoy. Whether you're looking to spend your days lounging on the beach, exploring the nearby attractions, or simply relaxing with your loved ones.

PRIVATE BEACH: BEACHFRONTS & BALCONIES @ NIANTIC
INSTANT BOOK: May 2026 - Jan 2027 = All Open Availability SUMMER 2026: June + July + Aug Steps away from CT Shoreline in back of beach house Amazing Views - Waterfront Both Balcony (year round) & Boardwalk Seating (2nd week May - until Nov 6th) *certain holidays/summer excluded in booking minimums/packages *discount applied to nightly rate only *we can not combine multiple discounts, yet highest % applies *if available, apply 10% non-refundable booking option

Sea Salt Air Changes Everything
Sea Salt Air Changes Everything... The mood. The conversation. The momentum. When you are here you will find yourself at the crossroads of nature and civilization. Stroll to a private association beach from this restful retreat. Stretch out on the deck overlooking swaying seagrass. Sing in the outdoor shower. Go on, no one is listening. Tasteful appointments. Elegance abounds. Salt life refined with the comforts that nourish your soul. Solitude awaits you.
Popular amenities for house rentals in Old Saybrook
House rentals with a pool

Breathtaking home with unforgettable views & pool!

Private Oasis W/Stunning Vinyard and Pool Views

Private & Pristine with Pool and Kid’s Playard

FREE Private Indoor Heated Pool - Mystic Home

Pool, 1 block to water, 8 mins to Main Street

Hot Tub~Pool~GameRoom~FirePit~BBQ~King Bed~Casinos

Secluded Farmhouse - Studio Apartment Style Unit

Port Jefferson Convenient, Cozy and Chic!
Weekly house rentals

15 acres! * Pine Pond at Devils Hopyard State Park

Adorable Beach House on LI Sound

Beachside Bliss w/ Game Room, Gym & Golf Green

Adorable Cottage with porch, walk to water & town

Sunset Skies | filmed for TV+walk to Water’s Edge

Money Point Beach House- Deck+Views + Beach Access

Summer is Calling! Book The Winding Rock House!

3BR Waterfront Oasis on Joshua Cove, Private Beach
Private house rentals

Stunning house on CT river !

SeaStar Beach House

Guilford Field House

Quarry House: Mid-Century Modern

Soundscape Beachfront House!

Woodland A-Frame

4 Bedrooms Modern Home with Water View & Access

Mulberry Seaside Cottage
When is the best time to visit Old Saybrook?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $403 SGD | $355 SGD | $391 SGD | $384 SGD | $434 SGD | $501 SGD | $501 SGD | $501 SGD | $443 SGD | $412 SGD | $379 SGD | $380 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 2,490 verified reviews to help you choose

Family-friendly holiday rentals
80 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
90 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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- Beachfront rentals Old Saybrook
- Rentals with beach access Old Saybrook
- Family-friendly rentals Old Saybrook
- Rentals with a firepit Old Saybrook
- Rentals with outdoor seating Old Saybrook
- Beach house rentals Old Saybrook
- Waterfront rentals Old Saybrook
- Rentals with a washing machine and dryer Old Saybrook
- Rentals with a fireplace Old Saybrook
- Pet-friendly rentals Old Saybrook
- Rentals with a patio Old Saybrook
- Cottage rentals Old Saybrook
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