Old Saybrook Holiday Rentals

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Holiday Rentals in Old Saybrook

adorable ranch in beach community

10.0 out of 10, Exceptional, (44)
"Beautiful location, lovely neighbors. House is dated as seen in photos. "
adorable ranch in beach community

⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

9.8 out of 10, Exceptional, (127)
"We loved our stay!"
The price is AU$920
includes taxes & fees
26 Feb - 27 Feb
⚓Capt Nathaniel Clarke Historic Homestead🤵Weddings👰Reunions❤Magnificent Yard🐕

Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

9.6 out of 10, Exceptional, (33)
"Lovely little cottage in a pretty, quiet neighborhood. Once you find it down the little lane, it's a great location to be in. Not far from town and close to the water, we really enjoyed relaxing at the house and in the backyard. Highly recommend."
Driftwood Cottage @ Saybrook Point Marina, 2 King Beds

OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW

9.4 out of 10, Exceptional, (33)
"Our second stay at the cottage. We spent a long weekend and the weather cooperated. The house is quite quirky, but has a really pleasant feel at home vibe. Beds were very comfortable. Kitchen could use some updates, but was sufficient. (still need a new can opener) The porch overlooking the Sound is magical. Nice neighborhood. If you have one...bring a golf cart! Lots of golf carts about. Host is always pleasant, communicating through Vrbo. We hope to return again. Thank you Khalig Family...
OCEAN/BEACH FRONT, HUGE YARD, SUNSET VIEW

Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

9.8 out of 10, Exceptional, (26)
"When my hometown sib couldn't host, we rented here and had our family Thanksgiving! It was great!"
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included

New Haven Village Suites

3.0 star property
7.6 out of 10, Good, (2005)
"Easy fast check in"
The price is AU$160
includes taxes & fees
3 Mar - 4 Mar
New Haven Village Suites

Postcard Cabins Machimoodus

2.0 star property
10.0 out of 10, Exceptional, (6)
"I loved this escape from reality. This was a very quiet romantic getaway for Valentine’s Day. The place was very clean and had everything we needed from a fully equipped small kitchen to everything outdoors we would need for a campfire and making s’mores. I loved this place and can’t wait to come back for another romantic getaway."
Postcard Cabins Machimoodus

Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages

8.6 out of 10, Excellent, (26)
"I recently had the pleasure of spending time at a vacation house in Stonington, Connecticut, and I cannot express enough how fantastic our stay was. This property exceeded all of our expectations and provided our family with a truly memorable experience.From the moment we arrived, we were captivated by the stunning water views. The house is perfectly situated to showcase the beauty of the surrounding landscape, and we found ourselves mesmerized by the sunsets over the water each evening. It was...
Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages

Lakeside cottage overhanging the water, beautiful window views across the lake

9.8 out of 10, Exceptional, (195)
"We stayed here as it was close to our daughters cheer Comp and it happened to be my husbands birthday weekend so we wanted to stay somewhere other than a hotel. We enjoyed the hot tub! The view of the lake, the fire pit, the spacious downstairs to watch tv and play family games! Very easy check in. Would recommend, we’d like to come back when weather is warmer to enjoy the lake "
The price is AU$428
includes taxes & fees
25 Feb - 26 Feb
Lakeside cottage overhanging the water, beautiful window views across the lake

Amazing Ocean Front 2 Story Home, Steps Away From The Water

9.8 out of 10, Exceptional, (90)
"The property was perfect for our vacation with amazing views. I was born & raised in Westerly but moved away. My family still lives in the area & my husband’s lives about 1-1/2hrs away. We flew in to spend Xmas w/our family & hosted Xmas day at the house. It was just what we needed. Big open floor plan, beautiful view of the beach & family. Also Cynthia was amazing!! She put up a tree for us, answered any questions we had, took care of emptying the trash/recycling when full & even let us extend...
Amazing Ocean Front 2 Story Home, Steps Away From The Water

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 star property
9.8 out of 10, Exceptional, (38)
"Great location. Nice place. Noisy neighbors though"
Luxury Furnished Apartments by Hyatus Downtown at Yale

Beautiful 2 Bedroom Boho Retreat in Downtown Mystic

10.0 out of 10, Exceptional, (22)
The price is AU$309
includes taxes & fees
27 Feb - 28 Feb
Beautiful 2 Bedroom Boho Retreat in Downtown Mystic

Classic East Hampton 5 BR in Private Beach Community.Pool, HotTub & Pirate Ship

10.0 out of 10, Exceptional, (80)
"The property was exactly as explained and all in our group loved the place. The house was clean and spacious with plenty of space to rekax."
Classic East Hampton 5 BR in Private Beach Community.Pool, HotTub & Pirate Ship

Charming Historic House in Downtown Mystic

10.0 out of 10, Exceptional, (129)
"This was a 10 out of 10 stay for us. The home was immaculate, stocked with everything you could need to feel at home. Very comfy beds and linens. Fantastic location and great hosts. Would definitely stay at this home again."
The price is AU$516
includes taxes & fees
24 Feb - 25 Feb
Charming Historic House in Downtown Mystic

3-bedroom vacation home just a 5-min walk to Main Street, Mystic

10.0 out of 10, Exceptional, (57)
"We had a great stay. The house in beautiful and very clean. Beds are all comfy and bedding top notch! Owners were very pleasant to text with and responsive. The location is great. Only issue may be with some who go to bed early as the bar next door is a little noisy up until midnight. Thanks for sharing your lovely home with us!"
3-bedroom vacation home just a 5-min walk to Main Street, Mystic

Private Guest House w/ Deck + Spectacular Views!

10.0 out of 10, Exceptional, (25)
"Meetings with friends who were staying at Mohegan Sun which was 20 minutes away. Pretty views, comfortable property. Would definitely return "
Private Guest House w/ Deck + Spectacular Views!

Spacious 7-bedroom house Stonington with amazing views.

Spacious 7-bedroom house Stonington with amazing views.

Oceanfront Beach House lay in bed and hear the waves, boats , birds

10.0 out of 10, Exceptional, (18)
"Very fun location near the beach. Beach is small but really a nice place to be. House worked well for our family of 4. Sun room was very nice."
Oceanfront Beach House lay in bed and hear the waves, boats , birds

Lakeside cottage ON the water with beautiful views up the lake!

9.8 out of 10, Exceptional, (171)
"We came for a couple of days for my son’s birthday and even though it was winter with the lake frozen over, there were still many options to keep us occupied all while staying warm and cozy. Definitely want to make a trip back for the summer!"
The price is AU$408
includes taxes & fees
25 Feb - 26 Feb
Lakeside cottage ON the water with beautiful views up the lake!

The Hemingway Carriage House - Romantic & Private Downtown Mystic Getaway

10.0 out of 10, Exceptional, (118)
"Great getaway. Enjoyed the stay tremendously. "
The Hemingway Carriage House - Romantic & Private Downtown Mystic Getaway
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Other types of properties in Old Saybrook you may be interested in

Pier Blue Inn Old Saybrook - Essex

2.0 star property
7.6 out of 10, Good, (918)
"Perfect place for our short stay, super clean and comfortable!"
The price is AU$125
includes taxes & fees
24 Feb - 25 Feb
Pier Blue Inn Old Saybrook - Essex

Saybrook Point Resort & Marina

3.5 star property
9.4 out of 10, Exceptional, (1000)
" Beautiful & excellent service. Needs regular soap."
The price is AU$518
includes taxes & fees
10 Mar - 11 Mar
Saybrook Point Resort & Marina

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.6 out of 10, Good, (1003)
"Coming back from a late concert at the Kate and this place was close by. The employees were very nice and the rooms were in great shape. The heat/ac was working very well; our room was around 75 degrees our entire stay. No problems checking out either. "
The price is AU$158
includes taxes & fees
16 Mar - 17 Mar
Quality Inn Old Saybrook - Westbrook
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Frequently asked questions

Can I find a holiday rental in Old Saybrook?

Yes, there are holiday rentals in Old Saybrook close to Saybrook Country Barn, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the popular beaches and shops in Old Saybrook. Allow some time to check out the spas during your trip.

What are some of the best holiday rentals that Old Saybrook has to offer?

Adorable ranch in beach community: This highly rated holiday home rental in Old Saybrook is located near the beach, and has a patio, a BBQ and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

How many holiday rentals will I find in Old Saybrook?

Choose from 59 Expedia holiday rentals in Old Saybrook for a memorable holiday.

What’s there to see and do in Old Saybrook?

Family-friendly attractions include Saybrook Country Barn and Stay and Play LLC, whereas Harvey's Beach and Connecticut River are a couple of great spots to enjoy the outdoors. Other places in town to visit include Katharine Hepburn Cultural Arts Center and Essex Saybrook Antique Village Shopping Center.

What’s a holiday rental in Old Saybrook like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Old Saybrook. Holiday rentals feature extras such as laundry facilities and kitchens so you'll have all the comforts of home. If you're concerned about a sanitised environment, holiday rentals can offer a sense of security away from public hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great choice for a small group gathering.