
Holiday houses in Old Saybrook
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Quick stats about holiday rentals in Old Saybrook

Total holiday rentals
Explore 130 holiday rentals in Old Saybrook

Nightly prices starting at
Old Saybrook holiday rentals start at $87 NZD per night before taxes and fees

Verified guest reviews
Over 4,230 verified reviews to help you choose

Family-friendly holiday rentals
110 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 40 rentals that welcome pets

Rentals with dedicated workspaces
60 properties have a dedicated workspace

Wi-Fi availability
120 of Old Saybrook holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Gym, BBQ and Laptop-friendly workspace across Old Saybrook rentals

4.9 Average rating
Old Saybrook stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated holiday rentals in Old Saybrook
Guests agree: these stays are highly rated for location, cleanliness and more.

Beachfront Paradise
Beautiful beachfront home available weekly in season third week of June through Labor Day) 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, 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.
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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
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Beachfront Home with Amazing Views | 5BR Sleeps 11
Welcome to "The Belaire Cottage" a spacious 5-bedroom beachfront retreat in the heart of the Saybrook Manor beach community. This charming New England coastal home offers the perfect blend of classic shoreline charm and modern comfort, with direct beach access right out the back door. The home features bright living spaces, coastal character, and plenty of room for families and groups to relax and unwind. Enjoy scenic shoreline walks, nearby beaches, and everything the Connecticut coast has to
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White Bird Beachfront. Dock available extra.
Enjoy quality time with your loved ones at White Bird, a tranquil beachfront home perfect for family getaways. Fall asleep to the soothing sound of the ocean waves .. The loft has a king bed, providing extra sleeping space for guests. The house is fully stocked with everything you need for a comfortable stay. Create lasting memories with your family at White Bird, where you can enjoy beach activities, and cozy bonfires. Please store stand up boards/kayak. If missing, they will be $150 each.
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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.
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Seas the Day at the CT Shoreline
Welcome to a slice of heaven by the water. Spacious 4BR updated beach cottage. Well-equipped kitchen, outdoor shower & gas grill. Sunny enclosed porches downstairs & upstairs. 2 decks for friends & family to stretch out while dining al fresco or simply lounging. 5 minute walk to 2 private beaches & 3 miles to 2 town beaches & the center for unique shops & eateries. Plus... fiber optic wifi, free coffee bar, games, bikes, beach toys, beach wagon & umbrellas. Spas, outlets & casinos nearby.
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Waterfront Oasis 4Bdr/2b
Direct oceanfront - pure paradise at the beach! Spectacular views of Long Island Sound with a large, partially covered, patio and private steps to the water/sand. Master bedroom with a wall of windows facing the water...wake up each morning to magnificent views. A slider to the waterside patio connects indoor and outdoor living. Dine alfresco, listen to the sound of the waves,watch the sunset - it is truly magnificent as the sun fades into the horizon and the sky illuminates with color.
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The Saybrook Point Bungalow, Stroll to Downtown
Charming 2-bedroom cottage in Old Saybrook Point neighborhood, just a 1-mile sidewalk stroll to Main Street shops and restaurants. The primary bedroom features a king bed that can convert to two XL twins upon request, plus a second bedroom with a twin. A large couch can sleep a fourth guest. Enjoy warm, modern touches throughout, a Smart TV in the living room, a sunny back porch, and a quiet yard perfect for morning coffee or relaxing after a day exploring this beautiful beach town.
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Beautiful View Cottage
Welcome to "Belle Vue Cottage". This charming and inviting cottage is located in a quiet and peaceful neighborhood in the South Cove area of Old Saybrook. Spend your days relaxing at Harvey's Beach, perusing the shops and restaurants along Main Street, taking in a show at The Kate, and unwind at the end of the day in your backyard oasis equipped with an outdoor TV and fire pit. We are less than a mile from Saybrook Point Inn and Spa, and 10 minutes to Water's Edge Resort and Spa.
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Hot Tub & Firepit•Sunsets & Beach Walk | Fireplace
Explore our Old Saybrook retreat on Great Hammock Rd, a cozy spot near the beach. Perfect for romance or family fun, it boasts stunning views and amenities. Relax in the hot tub, use bikes for local exploration, and enjoy evenings by the fire pit. Indoors, a fireplace adds warmth. Book now for a delightful getaway with views, memories, and the charm of Old Saybrook! Please note Our property is strictly an animal-free zone due to severe allergies persisting in the family.
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Private apartment in the heart of Old Lyme village
This rare village gem is located in the heart of historic Old Lyme, CT. The freshly renovated two bedroom apartment with private entry is a quick walk to the historic arts community, a block from the river for exploring and a quick ride to lake or beach. The property features various flower and vegetable gardens with a stunning pergola and patio for outdoor dining. Conveniently located off I-95 to access nearby quaint New England waterside towns, shops and restaurants.
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Ideal Historic Home in Essex Village
Welcome to village life in the heart of Essex Village. This is the longest running and most visited vacation rental home on Main St in Essex, CT. Chosen as the best small town in America by Norman Crampton in his book, The 100 Best Small Towns in America. Essex also appears in 1000 Places to Visit Before You Die. Located on the Connecticut River, this friendly New England community has been welcoming travelers since before the American Revolution.
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Popular amenities for Old Saybrook holiday rentals
Other great holiday rentals in Old Saybrook

Osprey Cozy Cottage | Near Downtown & Beaches
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Sunrise Beach Cottage
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Water Views and Walk to Beach
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Newly renovated CT shoreline home next to Marinas
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Luxury Driftwood Cottage @ Saybrook Point
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Addison's Oasis
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Adorable single story cottage-by-the-sea
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Captain Clark Historic Homestead Spacious Retreat
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When is the best time to visit Old Saybrook?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $487 NZD | $478 NZD | $487 NZD | $489 NZD | $567 NZD | $619 NZD | $577 NZD | $584 NZD | $536 NZD | $501 NZD | $501 NZD | $520 NZD |
| 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 |
Frequently Asked Questions
What are the best places to stay in Old Saybrook?
Old Saybrook has accommodations near the shoreline, around Main Street, and just outside the Connecticut River. Areas near the beach and the town center help guests explore local shops, dining, and water activities.
What are the best things to do in Old Saybrook with kids?
Families often explore sandy beaches, playgrounds, and nature centers around Old Saybrook. The town has an ice cream shop, waterfront parks, and easy trails that are great for younger travelers.
What are some of the best things to do in Old Saybrook?
Old Saybrook has sandy beaches, peaceful marshes for exploring by kayak, and a lively Main Street with local shops and galleries. The town also has historic sites and a theater for those interested in arts and culture.
How is the weather in Old Saybrook?
Old Saybrook has cold winters near 24–38°F (-4–4°C), with possibilities of snow, and warm summers that reach 68–83°F (20–29°C). Rain falls throughout the year, so a waterproof layer is useful for all seasons.
When is the best time to visit Old Saybrook?
Late spring through early fall is often recommended for visiting Old Saybrook, with warmer afternoons near 60-83°F (15-29°C), blooming landscapes, and outdoor events. Colder months have a quieter atmosphere for those seeking a slower pace.
What are the best places to visit in Old Saybrook?
Visiting the Katharine Hepburn Cultural Arts Center, the Lynde Point Lighthouse, and Main Street’s shops are often recommended in Old Saybrook. Local nature parks invite exploration year-round.
What are some hiking trails in Old Saybrook?
Explore the Fort Saybrook Monument Park for a short historical stroll or the trails at The Preserve for woodland walks. Local marsh paths are great for spotting birds and quiet reflection.
What are some family activities we can do in Old Saybrook?
Old Saybrook has family-friendly mini golf, interactive art workshops, and public parks for picnics or kite flying. Kids often enjoy exploring tidal pools or taking boat rides on the nearby river.
What are some of the best day trip ideas from Old Saybrook?
Explore nearby coastal villages, nature reserves, or historic lighthouses for a change of scenery. Many explore local vineyards or visit neighboring small towns known for museums and maritime history.
Are there any pet friendly accommodations available in Old Saybrook?
Many stays in Old Saybrook welcome pets, especially near the beach and in residential neighborhoods. Filter options when searching to find spaces with pet-friendly amenities.
What are some local tips for visiting Old Saybrook?
Locals suggest packing in layers to adjust for changing weather and exploring beyond Main Street for shops, marsh walks, and cozy cafes. Consider bringing a bike or renting a kayak for a new perspective on the inlets and coastal scenery.
What is Old Saybrook known for?
Old Saybrook is known for its maritime history, sandy beaches, and small-town New England charm. The town’s connection to Katharine Hepburn and its classic Main Street culture are often highlighted.
What are the best hidden gems to explore in Old Saybrook?
Old Saybrook has quiet marsh trails, lesser-known art galleries, and historic cemeteries that reflect centuries of local stories. Small waterfront parks and tucked-away bookshops are often suggested for a peaceful break.
What are the best foods to try in Old Saybrook?
Seafood is frequently suggested—look for dishes featuring fresh clams, lobster rolls, or locally caught fish. Old Saybrook also has bakeries known for pies and seasonal local produce.
What should I bring for a trip to Old Saybrook?
Pack layers for changing weather, comfortable shoes for exploring marshes or Main Street, and a hat for sun protection in summer. A rain jacket can be useful, especially in spring or fall.
What is the nightlife in Old Saybrook like?
Old Saybrook has a laid-back nightlife scene, with casual pubs, wine bars, and some spots featuring live music. Some evenings include community performances or small theater shows around Main Street.
What are the most popular events or festivals in Old Saybrook?
Seasonal festivals with art, music, and food pop up around Main Street in the summer and early fall. Holiday parades, craft fairs, and outdoor concerts are frequently suggested community gatherings.
Are there family friendly vacation rentals in Old Saybrook?
Many vacation rentals around Old Saybrook are family friendly, with extra bedrooms, outdoor spaces, and proximity to beaches or playgrounds. Listings often include amenities like full kitchens and laundry.
Destinations to explore
- Yale University
- Mohegan Sun
- Foxwoods Resort Casino
- East Matunuck State Beach
- Cooper's Beach, Southampton
- Fairfield Beach
- Ocean Beach Park
- Charlestown Beach
- Mystic Seaport Museum
- Mystic Aquarium
- Southampton Beach
- University of Connecticut
- University of Rhode Island
- Soundview Beach
- Hammonasset Beach State Park
- Powder Ridge Mountain Park & Resort
- Wölffer Estate Vineyard
- Ocean Beach
- Sleeping Giant State Park
- Ski Sundown
- Meschutt Beach
- Orient Beach State Park
- Ditch Plains Beach
- Wesleyan University





