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.

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Guest favorite

Home in Lyme

4.97 out of 5 average rating, 189 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.

May 5 – 12

G$58,717 GYD per night

Guest favorite

Apartment in Chester

4.95 out of 5 average rating, 313 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!

Apr 15 – 22

G$41,342 GYD per night

Guest favorite

Home in East Lyme

4.96 out of 5 average rating, 104 reviews

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.

Mar 1 – 8

G$31,649 GYD per night

Guest favorite

Cottage in Groton

4.94 out of 5 average rating, 139 reviews

EASY BEAT

LOVELY MID 1800'S COTTAGE Located in the historic Groton Bank neighborhood. Close to beaches, casinos, walking distant to EB. Short drive to Pfizer, Coast Guard Academy, Connecticut College, US Submarine Base and minutes to downtown Mystic. This property is a one bedroom one bath with a single pullout couch in bedroom and living room. Offers a spacious outside lawn with patio. Lots of off street parking. Fenced yard for pets. New Central Air and heat. Washer, dryer, grill and fire pit.

Feb 18 – 25

G$32,333 GYD per night

Guest favorite

Cottage in Chester

4.98 out of 5 average rating, 229 reviews

Updated cottage "Beriozka" on Cedar Lake

Originally from Russia (hence the name “Beriozka” meaning Birch Tree) I live in Stamford CT. About 7-8 years ago I’ve discovered Chester/ Essex area and fell in love. I’ve been coming here during summer to enjoy river rides, during winter just to see snow on the ground of old towns and needless to say during fall – when all the beauty of nature unfolds. Then came an idea to have an own place here and when an opportunity came to buy this small cottage on Cedar Lake I’ve jumped on it.

Dec 1 – 8

G$44,302 GYD per night

Guest favorite

Apartment in Groton

4.95 out of 5 average rating, 147 reviews

Cozy Studio with water views

Studio apartment with private entrance overlooking the Thames River. Beautiful sunsets in this cozy space. Has a Queen size bed, small dining table, desk, Galley kitchen with two burner stove, microwave, refrigerator and kuerig, toaster and toaster oven. Laundry can be used for longer stays (4 or more days) Towels and Linens provided. Beach chairs & towels available upon request. Outdoor space equipped with patio furniture, umbrella, and a grill for the warmer months.

Jan 18 – 25

G$24,265 GYD per night

Guest favorite

Apartment in East Haddam

4.89 out of 5 average rating, 106 reviews

Penny Corner Airbnb

My place is located up the hill from Good Speed Opera House. The Opera House is on the same side of the river as my place. The folklore is that vacationers used to pay a penny to have their belongings transported by ox and wagon from the port at the river to this corner. A two family home built in 1884. The space is a ground level 1 bedroom apartment with private entrance. There is no TV in the unit, WIFI is available for your devices.

Oct 13 – 20

G$21,413 GYD per night

Guest favorite

Barn in Essex

4.98 out of 5 average rating, 124 reviews

River Barn, Sidewalk Stroll into Essex Village

The Coolest Airbnb in Connecticut (Conde Nast Traveler 2021) The barn is a perfect retreat. Ideal for those looking to take a break from city life or those working remotely. Would also make for a lovely place to call home while you are selling or renovating your own home. Couples, two good friends, singles, or a family with an older child will enjoy the configuration. It will also make for a lovely getaway for a couple with a newborn.

Aug 8 – 15

G$149,434 GYD per night

Guest favorite

Guesthouse in Mystic

4.99 out of 5 average rating, 541 reviews

Gorgeous Waterfront Getaway

Perfect getaway from the city for couples wanting peace and tranquility and stunning views. A beautiful waterfront one bedroom guesthouse, one and one-half miles from downtown Mystic CT. Beautifully decorated with art and antiques. Kitchenette, full bath and loft bedroom. Queen bed. Air conditioning and heated. Belgian linen bedding! Private patio. Dock. Kayak/Canoe rentals close by. Internet.

Nov 23 – 28

G$38,135 GYD per night

Guest favorite

Home in Old Lyme

4.94 out of 5 average rating, 257 reviews

Modern Luxurious CT Country Home

Beautiful mid-century modern glass and wood house in the forest, featuring tranquil designer spaces and continuously updated amenities. With only 2 hours from New York City and Boston, by train or by car, this is the ideal sanctuary for a perfect getaway. Minimum 2 nights during fall through spring months, 3 to 5-nights minimum in the summer months.

Oct 15 – 22

G$85,389 GYD per night

Guest favorite

Apartment in Deep River

4.83 out of 5 average rating, 172 reviews

Loft apartment, deck and great water view

Great location, walk to town & only steps to the Connecticut River. Great for train aficionados- you can watch and photograph the famous Essex steam train in action.This historic factory built in 1874 has manufactured sails, metal objects and lastly Lace. Enjoy your private comfortable apartment with river views and deck.

Jan 23 – 30

G$24,036 GYD per night

Guest favorite

Home in Old Lyme

4.96 out of 5 average rating, 125 reviews

Modern Farmhouse with Hot Tub in Old Lyme, CT

Originally built in 1856 this farmhouse has been lovingly restored with stylish and modern amenities for a perfect vacation getaway. Nestled in the heart of downtown, historic Old Lyme the property is convenient to shops, restaurants and local shoreline activities including water sports and hiking.

Apr 11 – 18

G$82,151 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Old Saybrook vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

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

Other great vacation rentals in Old Saybrook

Guest favorite

Home in Old Saybrook

4.96 out of 5 average rating, 104 reviews

Year Round Beach House in Old Saybrook, CT.- Pets

Oct 13 – 20

G$79,556 GYD per night

Guest favorite

Guest suite in New Haven

4.99 out of 5 average rating, 157 reviews

Cozy cottage in historic neighborhood

May 8 – 15

G$31,205 GYD per night

Guest favorite

Guest suite in Wallingford

5.0 out of 5 average rating, 499 reviews

Wintergreen Gardens Suite @ William Becroft House

Aug 6 – 13

G$18,201 GYD per night

Guest favorite

Guest suite in Old Saybrook

5.0 out of 5 average rating, 37 reviews

Cozy Loft Getaway

May 6 – 13

G$32,672 GYD per night

Guest favorite

Cottage in Westbrook

4.86 out of 5 average rating, 94 reviews

Peaceful Riverfront Cottage w/Dock, Walk to Beach

Oct 13 – 20

G$28,414 GYD per night

Guest favorite

Cottage in Old Saybrook

5.0 out of 5 average rating, 13 reviews

Little cottage of gratitude

Nov 15 – 22

G$36,499 GYD per night

Guest favorite

Loft in Westbrook

5.0 out of 5 average rating, 60 reviews

Lovely one bedroom studio with on-site parking.

Jan 5 – 12

G$29,866 GYD per night

Guest favorite

Cottage in Old Saybrook

4.95 out of 5 average rating, 44 reviews

1920’s charming dollhouse near South Cove

Feb 13 – 20

G$49,840 GYD per night

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Other great vacation rentals in Old Saybrook

Guest favorite

Guesthouse in Madison

5.0 out of 5 average rating, 58 reviews

The Barn by the Sound

Dec 17 – 24

G$34,512 GYD per night

Guest favorite

Home in Old Saybrook

4.98 out of 5 average rating, 48 reviews

Steps to Beach! *Cozy Cottage* Pet Friendly

Jun 1 – 8

G$64,973 GYD per night

Guest favorite

Cottage in Old Saybrook

4.97 out of 5 average rating, 75 reviews

Beautiful Cottage View

Jan 7 – 14

G$64,654 GYD per night

Guest favorite

Home in Westbrook

5.0 out of 5 average rating, 27 reviews

Sea Salt Air Changes Everything

Sep 4 – 11

G$68,287 GYD per night

Guest favorite

Home in Old Saybrook

5.0 out of 5 average rating, 24 reviews

3BR Private Cottage w/ Pool in Old Saybrook

Sep 9 – 16

G$100,960 GYD per night

Guest favorite

Home in Old Saybrook

5.0 out of 5 average rating, 7 reviews

Waterfront home

Aug 19 – 26

G$226,131 GYD per night

Guest favorite

Home in Haddam

5.0 out of 5 average rating, 76 reviews

Cozy Comforts!

Dec 14 – 21

G$22,472 GYD per night

Guest favorite

Cottage in Westbrook

4.99 out of 5 average rating, 79 reviews

The Old Salt Cottage · Cozy Gateway Near Beach

Dec 19 – 26

G$116,193 GYD per night

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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
90 properties are a good fit for families
Total number of reviews
2.7K reviews
Nightly prices starting at
G$10,424 GYD before taxes and fees

Frequently Asked Questions

What are the most popular amenities for House Rentals in Old Saybrook?
Enhance your stay in our House Rentals with the most popular amenities: over 70 homes with air conditioning, over 70 homes with wifi, over 40 homes with a bbq area, over 10 homes with a gym, and more. Indulge in the ultimate retreat, tailored to your preferences.
Are there house rentals with a dedicated workspace in Old Saybrook?
Yes! Work meets play with ease at over 40 house rentals in Old Saybrook featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do cottage rentals in Old Saybrook have wifi?
Absolutely! We offer over 10 cottage rentals with wifi in Old Saybrook. Enjoy a tailored experience with all the comforts you desire.
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.
How much does it cost to stay in house rentals in Old Saybrook?
Experience the best of Old Saybrook with our house rentals, starting at about $100 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cottage rentals in Old Saybrook have air conditioning?
Absolutely! We offer over 10 cottage rentals with air conditioning in Old Saybrook. Enjoy a tailored experience with all the comforts you desire.
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.

Old Saybrook vacation rentals

Top-rated vacation rentals in Old Saybrook

Vacation rentals for every style

Cottages

Houses

Hotels

Popular amenities for Old Saybrook vacation rentals

Stay near Old Saybrook's top sights

Other great vacation rentals in Old Saybrook

Home in Old Saybrook

Guest suite in New Haven

Guest suite in Wallingford

Guest suite in Old Saybrook

Cottage in Westbrook

Cottage in Old Saybrook

Loft in Westbrook

Cottage in Old Saybrook

Other great vacation rentals in Old Saybrook

Guesthouse in Madison

Home in Old Saybrook

Cottage in Old Saybrook

Home in Westbrook

Home in Old Saybrook

Home in Old Saybrook

Home in Haddam

Cottage in Westbrook

Quick stats about vacation rentals in Old Saybrook

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

What are the most popular amenities for House Rentals in Old Saybrook?

Are there house rentals with a dedicated workspace in Old Saybrook?

Do cottage rentals in Old Saybrook have wifi?

Do house rentals in Old Saybrook have a gym?

Do house rentals in Old Saybrook have a bbq area?

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

Do cottage rentals in Old Saybrook have air conditioning?

Are there family-friendly cottage rentals in Old Saybrook?

Destinations to explore