Old Saybrook vacation rentals

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Top-rated vacation rentals in Old Saybrook

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

Guest favorite

Home in Lyme

4.97 out of 5 average rating, 185 reviews

“The Answer” Tidal River-Kayaks Fire pit Fireplace

“The Answer” is listed amongst the 15 best Airbnbs in Ct, from Travellers Worldwide 2022 and 2023 and featured in “Only In Your State” titled “This Riverfront House Will Be Your New Favorite” February 2024 Kayaks included This unique glass-front, tidal river retreat, is privately nestled on historic Hamburg Cove. It offers gorgeous year-round, tranquil water and valley views. Extraordinarily and serene. The interior is open/spacious and bathed in light. Wake up to the many sounds of nature.

Sep 28 – Oct 5

ﺩ.ﺇ1,250 per night
Guest favorite

Apartment in Chester

4.95 out of 5 average rating, 309 reviews

Chester Village 'Pied-à-terre' above art gallery

If finding a place in an ideal location w/ thoughtful design matters to you, then you've found it! Sunshine filled living room w/ high ceilings, a private bedroom in back w/ large private deck overlooking Pattaconk Brook. Our place is a gem, and set up for the comfort of our guests. Located in the heart of Chester Village, above our art gallery & boutique, and neighbor to some of the BEST restaurants, art and shopping in CT! NEW! Winter weekdays - ONE night stays are now available - message us!

Oct 15 – 22

ﺩ.ﺇ746 per night
Guest favorite

Cottage in Waterford

4.99 out of 5 average rating, 104 reviews

Classic CT Cottage w/ Trail by Harkness Park/Ocean

Tastefully appointed! A quaint cottage in a forest setting on 6 acres bordering Harkness State Park. A peaceful & serene setting where you can hear nature by day and the lighthouse sound signal at night. The cottage is fully equipped & very comfortable for your stay. The Waterford beach is a short drive away...less than 2 miles through the forest...as are beautiful hikes along the coast. Centrally located near Historic Mystic, Niantic, Conn College, US Coast Guard Academy & the US Naval Base.

Apr 12 – 19

ﺩ.ﺇ556 per night

Popular amenities for Old Saybrook vacation rentals

Stay near Old Saybrook's top sights

Saybrook Point Inn & Spa - Luxury Connecticut Oceanside Hotel21 locals recommend
Paperback Café12 locals recommend
Walmart23 locals recommend
Monkey Farm20 locals recommend
Cuckoo's Nest Mexican Food17 locals recommend
Little Pub Old Saybrook13 locals recommend

Old Saybrook cottage rentals

Guest favorite

Cottage in East Lyme

4.97 out of 5 average rating, 232 reviews

Your Nest Near The Beach

Sep 3 – 10

ﺩ.ﺇ919 per night
Guest favorite

Cottage in Riverhead

4.98 out of 5 average rating, 126 reviews

Savor Blazing Ocean Sunsets at a Soothing Beachfront Haven

Mar 26 – Apr 2

ﺩ.ﺇ2,735 per night
Superhost

Cottage in Scituate

4.9 out of 5 average rating, 193 reviews

5 Star cottage in historical Clayville

Apr 3 – 10

ﺩ.ﺇ362 per night
Guest favorite

Cottage in Waterford

4.99 out of 5 average rating, 106 reviews

Coastal Cottage Private Studio

Apr 8 – 15

ﺩ.ﺇ601 per night
Guest favorite

Cottage in Guilford

4.96 out of 5 average rating, 157 reviews

Luxury cottage by the sea with hot tub and pool

Feb 11 – 18

ﺩ.ﺇ1,229 per night
Guest favorite

Cottage in Voluntown

4.95 out of 5 average rating, 181 reviews

Lakeside Cottage in the Forest

Nov 23 – 30

ﺩ.ﺇ566 per night
Guest favorite

Cottage in Colchester

4.97 out of 5 average rating, 127 reviews

Lakefront peaceful getaway cottage

Nov 12 – 19

ﺩ.ﺇ824 per night
Guest favorite

Cottage in Middlefield

4.93 out of 5 average rating, 228 reviews

Lake Beseck cottage

Oct 1 – 8

ﺩ.ﺇ633 per night
Guest favorite

Cottage in South Kingstown

4.92 out of 5 average rating, 133 reviews

THE WHITECAP COTTAGE

Oct 12 – 19

ﺩ.ﺇ530 per night
Guest favorite

Cottage in Groton

4.95 out of 5 average rating, 269 reviews

Restored Historic Schoolhouse, Mystic River Views

Nov 4 – 11

ﺩ.ﺇ701 per night
Guest favorite

Cottage in Groton

4.99 out of 5 average rating, 146 reviews

Mind Over Mystic Cottage

Jul 17 – 24

ﺩ.ﺇ1,202 per night
Guest favorite

Cottage in Newtown

4.93 out of 5 average rating, 153 reviews

Private and Serene home close to I-84 and shopping

Mar 24 – 31

ﺩ.ﺇ507 per night

Old Saybrook beach vacation rentals

Guest favorite

Guesthouse in Mystic

4.99 out of 5 average rating, 535 reviews

Gorgeous Waterfront Getaway

Oct 5 – 10

ﺩ.ﺇ662 per night
Guest favorite

Guesthouse in Groton

4.94 out of 5 average rating, 381 reviews

Quiet studio with sleeping loft and deck

Jul 9 – 16

ﺩ.ﺇ448 per night
Guest favorite

Home in East Lyme

4.96 out of 5 average rating, 161 reviews

Beachfront Paradise

Nov 19 – 26

ﺩ.ﺇ1,581 per night
Guest favorite

Guest suite in Cutchogue

4.88 out of 5 average rating, 582 reviews

Walk to Vineyards, Beaches, Farms & Town

Aug 27 – Sep 3

ﺩ.ﺇ595 per night
Guest favorite

Townhouse in Westbrook

4.92 out of 5 average rating, 184 reviews

Wake up with views of the ocean

Apr 12 – 19

ﺩ.ﺇ973 per night
Guest favorite

Home in Clinton

4.96 out of 5 average rating, 171 reviews

Waterside Beach Retreat

Dec 11 – 18

ﺩ.ﺇ1,173 per night
Guest favorite

Apartment in New London

4.89 out of 5 average rating, 262 reviews

The Whaler’s Loft · Ocean Beach, Mystic & USCGA

Apr 15 – 22

ﺩ.ﺇ572 per night
Guest favorite

Apartment in New London

4.98 out of 5 average rating, 288 reviews

Quiet Neighborhood home close to everything

Oct 23 – 30

ﺩ.ﺇ485 per night
Guest favorite

Home in Old Lyme

4.96 out of 5 average rating, 118 reviews

Cozy Beach Cottage with short walk to the beach

Feb 7 – 14

ﺩ.ﺇ1,121 per night
Guest favorite

Home in Groton

4.95 out of 5 average rating, 156 reviews

True Ocean Front Vacationing - Groton/Mystic

Jan 23 – 30

ﺩ.ﺇ1,683 per night
Guest favorite

Apartment in Milford

4.97 out of 5 average rating, 505 reviews

Water front studio apartment with fireplace.

Aug 27 – Sep 3

ﺩ.ﺇ738 per night
Superhost

Home in Greenport

4.94 out of 5 average rating, 136 reviews

Blue Bay Dream - Apt #2

Jan 23 – 30

ﺩ.ﺇ288 per night

Beach cottage rentals in Old Saybrook

Superhost

Cottage in Charlestown

4.88 out of 5 average rating, 125 reviews

Pet-Friendly Private Beach Oceanfront Cottage A/C

Dec 23 – 30

ﺩ.ﺇ1,972 per night
Guest favorite

Cottage in Montauk

4.91 out of 5 average rating, 511 reviews

Montauk Oceanview

Jul 24 – 31

ﺩ.ﺇ2,520 per night
Superhost

Cottage in Branford

4.86 out of 5 average rating, 195 reviews

Cozy Home In Short Beach Community

Nov 4 – 11

ﺩ.ﺇ608 per night
Guest favorite

Cottage in Mystic

4.98 out of 5 average rating, 206 reviews

Mystic Cottage Retreat, near downtown

Nov 11 – 18

ﺩ.ﺇ809 per night
Guest favorite

Cottage in Southold

4.9 out of 5 average rating, 151 reviews

Comfortable Cottage on the Great Pond near beach.

Mar 15 – 22

ﺩ.ﺇ1,044 per night
Guest favorite

Cottage in Montauk

4.87 out of 5 average rating, 216 reviews

Waterfront Cottage, Fort Pond MTK

Dec 11 – 18

ﺩ.ﺇ2,934 per night
Guest favorite

Cottage in Milford

4.96 out of 5 average rating, 230 reviews

Spring Sale! Cozy Cottage | Walk to Beach | Pet

Oct 14 – 21

ﺩ.ﺇ840 per night
Superhost

Cottage in Milford

4.88 out of 5 average rating, 134 reviews

Direct waterfront beach cottage

Oct 6 – 13

ﺩ.ﺇ1,792 per night
Guest favorite

Cottage in Riverhead

4.85 out of 5 average rating, 127 reviews

Affordable Wine Country Cozy Cottage

Jun 4 – 11

ﺩ.ﺇ1,162 per night
Superhost

Cottage in North Kingstown

4.87 out of 5 average rating, 161 reviews

5-STAR Cove Cottage near Newport - Walk to Beach

Aug 10 – 17

ﺩ.ﺇ1,509 per night
Guest favorite

Cottage in Rocky Point

4.93 out of 5 average rating, 143 reviews

Adorable cottage

Jan 31 – Feb 7

ﺩ.ﺇ676 per night
Superhost

Cottage in Port Jefferson

4.8 out of 5 average rating, 261 reviews

The Hilltop Harborview

Jul 31 – Aug 7

ﺩ.ﺇ3,492 per night

Quick stats about vacation rentals in Old Saybrook

Total rentals

110 properties

Rentals with dedicated workspaces

50 properties have a dedicated workspace

Pet-friendly rentals

40 properties allow pets

Family-friendly rentals

80 properties are a good fit for families

Total number of reviews

2.7K reviews

Nightly prices starting at

ﺩ.ﺇ184 before taxes and fees

Frequently Asked Questions

  • What types of vacation rentals are available in Old Saybrook?

    Uncover the perfect home-away-from-home with our diverse selection of vacation rentals in Old Saybrook. From over 20 cottage rentals to over 70 house rentals, we've got you covered. For even more variety, explore our Airbnb Categories to find the ideal space for your getaway.

  • Are there vacation rentals with a dedicated workspace in Old Saybrook?

    Yes! Work meets play with ease at over 50 vacation rentals in Old Saybrook featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • How much does it cost to stay in cottage rentals in Old Saybrook?

    Experience the best of Old Saybrook with our cottage rentals, starting at about $80 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Old Saybrook?

    Four-legged friends are welcome in Old Saybrook. Choose from more than 40 vacation rentals for guests traveling with pets.

  • Are there family-friendly cottage rentals in Old Saybrook?

    Old Saybrook has more than 10 family-friendly cottage rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

  • Do house rentals in Old Saybrook have a gym?

    Absolutely! We offer over 10 house rentals with a gym in Old Saybrook. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Old Saybrook have a bbq area?

    Absolutely! We offer over 40 house rentals with a bbq area in Old Saybrook. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Old Saybrook have self check-in?

    Absolutely! We offer over 30 house rentals with self check-in in Old Saybrook. Enjoy a tailored experience with all the comforts you desire.

Destinations to explore