Old Saybrook Holiday Rentals

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Holiday Rentals in Old Saybrook

Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly

9.8 out of 10, Exceptional, (44)
"Amazing property and relaxing weekend! 😄 Host was accommodating and responded promptly. Disappointed with accuracy of listing regarding the spa tub and picture/listing of canoe. Planned a canoe day and was unable due to no canoe on property. Dog loved the yard and enjoyed her stay too! "
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly

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, (1981)
"It was good"
The price is AU$152
includes taxes & fees
25 Dec - 26 Dec
New Haven Village Suites

Mid-Century Fall Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

10.0 out of 10, Exceptional, (81)
"Very relaxing place to stay 2 minutes from the beach and fabulous sunsets. Property was spotless with tons of room. "
Mid-Century Fall Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!

Cliffside Resort Condominiums

3.0 star property
9.0 out of 10, Wonderful, (207)
"Stove it’s not efficient and refrigerator blocked with the corner of wall"
Cliffside Resort Condominiums

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

9.8 out of 10, Exceptional, (193)
"Our stay was great! Bobby was there when we arrived to show us around. The cottage was comfy and cozy. It was a great place to relax and enjoy the beauty of the water on either of the 2 decks or from the hot tub. The beds were comfortable "
The price is AU$431
includes taxes & fees
16 Jan - 17 Jan 2025
Lakeside cottage overhanging the water, beautiful window views across the lake

Private Guest House w/ Deck + Spectacular Views!

10.0 out of 10, Exceptional, (23)
"We loved our trip. The cottage is beautifully done and the views incredible. We appreciated the hospitality extended by our host (and Nico the dog!) and enjoyed exploring the nearby woodland. Our kids are already asking if we can go back and visit again. "
Private Guest House w/ Deck + Spectacular Views!

Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

10.0 out of 10, Exceptional, (13)
"This was a great spot to stay with my wife, another couple, and my dog! The house is small - especially downstairs. But it is extremely well thought out and space is used as effectively as can be. Upstairs had 2 good sized bedrooms with king beds and a nicely renovated bathroom with a great shower. The house is located in a small, cute, and a bit of an unusual neighborhood. Very quiet. Very safe feel. But not too good for much dog walking and parking is super tight. Owner was very good with...
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!

Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

7.2 out of 10, Good, (7)
"Stayed here for a weekend at Mystic with my parents who are older. Lots of steps from the street so bear in mind. Claude was very kind when I called him with questions and the water and fruit on the kitchen table was a nice touch. Neighborhood is a bit loud from front bedroom but beds were oh so cozy and again, CLEAN CLEAN CLEAN!"
The price is AU$446
includes taxes & fees
23 Dec - 24 Dec
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

70 Year old cottage on 2.8 acres, stunning views and sunsets

8.4 out of 10, Very good, (6)
"We all liove the various Connecticut shore towns, and Ild Lyme was delightful. We revisited some favorite spots, and discovered a few new ones. The vintage appliances were particularly nice to find, and looking at old photos, we realized that the original cottage was really 100 years old!"
70 Year old cottage on 2.8 acres, stunning views and sunsets

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

9.8 out of 10, Exceptional, (167)
"The Cottage was the perfectly cozy home away from home for our Thanksgiving trip to visit family. Everything was thought of from the towels for the hot tub, to the coffee for the morning. Thanks so much for such a lovely getaway for our family!"
The price is AU$503
includes taxes & fees
7 Jan - 8 Jan 2025
Lakeside cottage ON the water with beautiful views up the lake!

Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

10.0 out of 10, Exceptional, (30)
"Taylor accommodated an early check in for us and priced excellent information It was perfect "
The price is AU$547
includes taxes & fees
22 Dec - 23 Dec
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino

Cape Cod home in great location! Walk to downtown

9.4 out of 10, Exceptional, (142)
"The house was clean and had a cozy feel. Good location too, with a lot of restaurants/ neat stores nearby. I would definitely recommend this if you're looking to go on vacation to Connecticut."
Cape Cod home in great location! Walk to downtown

The Hemingway Carriage House - Romantic & Private Downtown Mystic Getaway

10.0 out of 10, Exceptional, (115)
"We loved our stay and plan to return. Very quiet, private, and walkable!"
The Hemingway Carriage House - Romantic & Private Downtown Mystic Getaway

Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

9.8 out of 10, Exceptional, (105)
"Lovely rental; very easy to work with property manager. Clean, close to ocean - would rent again"
The price is AU$866
includes taxes & fees
20 Dec - 21 Dec
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round

1.5 Acre Luxury Escape - Saltwater Pool with Water Views

10.0 out of 10, Exceptional, (1)
"Very nice house In great shape and outstanding pool area."
1.5 Acre Luxury Escape - Saltwater Pool with Water Views

Super Cute & Cozy Apartment in Downtown Mystic!

9.8 out of 10, Exceptional, (65)
"It is a cute, but tiny apartment. Very short walk to "downtown" Mystic and the Seaport. There is another apartment above it so at times you'll hear voices and footsteps. The heat hadn't been turned on, so the 1st nite was chilly but the property manager quickly addressed that."
The price is AU$300
includes taxes & fees
19 Jan - 20 Jan 2025
Super Cute & Cozy Apartment in Downtown Mystic!

Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

10.0 out of 10, Exceptional, (127)
"Although I went went it is cold the view and location were excellant. I can definately see taking advantage of this place during the summer. The host was responsive and available. "
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub

Beach House

9.8 out of 10, Exceptional, (49)
"Easy and seamless check in process. Home was comfortable and s"
Beach House

Unbeatable Downtown Mystic Location

9.8 out of 10, Exceptional, (140)
"The location, the charm of the unit is consistent with the Mystic Charm! Fabulous!"
The price is AU$650
includes taxes & fees
30 Dec - 31 Dec
Unbeatable Downtown Mystic Location
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

Quality Inn Old Saybrook - Westbrook

2.5 star property
7.6 out of 10, Good, (1001)
"Older property. Well kept. Clean stay."
The price is AU$158
includes taxes & fees
26 Dec - 27 Dec
Quality Inn Old Saybrook - Westbrook

Saybrook Point Resort & Marina

3.5 star property
9.4 out of 10, Exceptional, (1000)
"Staff greeted us right away- everyone was friendly and helpful, room was lovely, hotel was nicely decorated for the holiday season, food and service in the restaurant was excellent- would definitely stay again"
The price is AU$553
includes taxes & fees
5 Jan - 6 Jan 2025
Saybrook Point Resort & Marina

Pier Blue Inn Old Saybrook - Essex

2.0 star property
7.6 out of 10, Good, (896)
"Such a great place. Very convenient to everything. Lovely yard area with great views and even a barbecue. Would definitely come back. "
The price is AU$125
includes taxes & fees
26 Dec - 27 Dec
Pier Blue Inn Old Saybrook - Essex
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?

Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly: This highly rated holiday home rental in Old Saybrook is located near the beach, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

How many holiday rentals will I find in Old Saybrook?

Choose from 60 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.