Old Saybrook Holiday Rentals

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Holiday Rentals in Old Saybrook

Smart TV, fireplace, stereo
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
10.0 out of 10, Exceptional, (71)
"We loved this property. It’s open floor plan made it a great gathering place. Great location, clean and comfortable. Highly recommend"
Mid-Century Summer Retreat: Private Beach, Stunning Sunsets, and Chef's Kitchen!
Property grounds
Private Guest House w/ Deck + Spectacular Views!
10.0 out of 10, Exceptional, (11)
"Our floors were being refinished so we needed a place to stay for a week with our dog. The cottage was perfect for our needs, with plenty of space to walk our dog."
Private Guest House w/ Deck + Spectacular Views!
Aerial view
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
10.0 out of 10, Exceptional, (7)
"Adorable cottage with full kitchen, luxurious bathroom and comfiest beds!! Cutest cul de sac with friendly neighbors"
Family-Friendly Lakeside Cottage with Spectacular Sunset Views Pet-Friendly!
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Property grounds
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
10.0 out of 10, Exceptional, (2)
"This VRBO was very Comfortable. Old Rustic House thats Been Upgraded with Modern Accomodations. We felt Very Relaxed here. We cooked Dinner /Breakfast . and enjoyed some Livation. Sitting area outside was perfect. . and we slept well.. . The only thing we were surprised about was the On Street Parking for unloading. And the Stairs at the Entrance.. Not Handicap Accesibble. But, in the end.. We were very happy. And will stay again. No Problem"
The price is NZ$445
per night
22 May - 23 May
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
Indoor pool, a heated pool
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
10.0 out of 10, Exceptional, (13)
"We just returned and loved our time at the villa! We chose to stay here for 2 nights of concerts at Mohegan sun and could not have been happier! The property is clean, comfortable and has everythign you could need. The snacks and water were a welcomed treat! Taylor was so accomodating and we hope to return one day!"
The price is NZ$528
per night
19 May - 20 May
Peaceful Spa Villa Getaway - Hot Tub - 3 minutes to Mohegan Sun Casino
Exterior
The Hemingway Retreat - Romantic & Private Downtown Mystic Getaway
10.0 out of 10, Exceptional, (99)
"Not only is the cottage cute and clean, the location is perfect! We were so close to everything in Mystic! Our two young boys were even able to scooter (while we walked) to the downtown area of shops and restaurants. We loved the quiet side street and the bit of water view from the property. We will definitely stay here again!"
The Hemingway Retreat - Romantic & Private Downtown Mystic Getaway
Beach nearby, sun-loungers, beach towels
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
10.0 out of 10, Exceptional, (88)
"Positive experience, great location, and cozy accommodations for a centrally located family weekend."
Adorable New England Cottage, 2 min walk to Beach 🏖️, Available year round
Property grounds
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
10.0 out of 10, Exceptional, (110)
"I stayed at this amazing studio cottage with my girlfriend for 2 nights for her birthday. Our hosts, Liz and Adam were simply amazing. They allowed us an early check in and a late check out. Liz even brought out bicycles for us to use to tour around the neighborhood and ride along the shore line. Because it was my girlfriends birthday (or maybe they just do this), they had Prosecco and Orange Juice plus beer and cheese and other snacks for us when we arrived. The cottage is adorable, perfect...
Studio, Private Beach, Kayak, Paddle board, Pool, Hot tub
Fridge, microwave, oven, stovetop
Beautiful 2 Bedroom Boho Retreat in Downtown Mystic
10.0 out of 10, Exceptional, (9)
"Our family stayed here to do an overnight on Mystic. The owner was super helpful and communicative, making sure we had what we needed. My son loves the snacks that were left, and I personally was very happy to see my favorite creamer stocked in the fridge - unexpected surprise! Would happily stay here again, as my son's favorite part of our whole trip was the bed."
The price is NZ$454
per night
20 May - 21 May
Beautiful 2 Bedroom Boho Retreat in Downtown Mystic
Exterior
Walk To Downtown & Seaport!
10.0 out of 10, Exceptional, (30)
"This cozy, clean apartment couldn't be any more convenient! We visited without a car, and could walk to the Seaport Museum (3 minutes,) downtown (8 minutes,) and the Amtrak (14 minutes.) The apartment is cute, quiet, and comfortable, with good internet, a full-sized kitchen, and a washer/dryer. Recommend this for a visit to Mystic!"
Walk To Downtown & Seaport!
Fridge, microwave, oven, stovetop
Charming Historic House in Downtown Mystic
10.0 out of 10, Exceptional, (110)
"We were in the area for a visit to local college, and we splurged on an overnight. So glad we did! Spotlessly clean, beautifully restored historical property right in the heart of a neighborhood and in walking distance to downtown. Comfortable beds, art supplies, games, and a well-appointed kitchen. Our daughter didn’t choose the college, but we will be back just to stay here again! Thank you for a truly special property."
The price is NZ$641
per night
29 May - 30 May
Charming Historic House in Downtown Mystic
3 bedrooms, desk, iron/ironing board, WiFi
The Bay Cottage · Rocky Neck Park, Beach & Niantic
10.0 out of 10, Exceptional, (5)
"I booked this for a sister weekend. It was perfect for what we needed. It appears that the house was built to be a summer getaway, so it is pretty basic and no frills and comes with all the creaks and quicks of an older house. The living room is perfect for hanging out and the four chairs make it easy to rearrange to suit your needs. The kitchen is nicely stocked with everything you would need to stay with a family and the dining room is spacious enough to easily accommodate everyone staying...
The price is NZ$824
per night
20 May - 21 May
The Bay Cottage · Rocky Neck Park, Beach & Niantic
Lake
Renovated 1 BR getaway 1 block from Mystic River in Historic downtown!
10.0 out of 10, Exceptional, (165)
"Excellent location. Perfect for a couple or one person. Well-equipped. Will definitely stay again."
Renovated 1 BR getaway 1 block from Mystic River in Historic downtown!
Beach nearby, beach towels
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
9.8 out of 10, Exceptional, (38)
"Great place. Cozy cottage!"
Steps to the Beach, Cozy Year Round Cottage 🐾 Pet Friendly
View from property
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
9.8 out of 10, Exceptional, (22)
"Property exactly as described. What an amazing view and right on the beach. Great communication with host. Answered all our questions very promptly. Would definitely recommend."
Oceanfront Oasis Spacious 3-Bedroom, 2-Bath Retreat for 12 Linens Included
Pool
Lakeside cottage ON the water with beautiful views up the lake!
9.8 out of 10, Exceptional, (160)
"A traditional family lake cottage. Peaceful, quiet, and rented with love. Everything from the thoughtful little notes in the home to the paintings on the wall makes you feel cozy and welcomed. Everything you could need or want is provided. The hot tub under the stars, on the water is really the icing on the cake."
The price is NZ$491
per night
23 May - 24 May
Lakeside cottage ON the water with beautiful views up the lake!
Fridge, microwave, oven, stovetop
Super Cute & Cozy Apartment in Downtown Mystic!
9.8 out of 10, Exceptional, (47)
"Cute apartment in a gorgeous New England town! Walkable to restaurants. Thoughtful treats too!"
The price is NZ$373
per night
27 May - 28 May
Super Cute & Cozy Apartment in Downtown Mystic!
Property grounds
Unbeatable Downtown Mystic Location
9.8 out of 10, Exceptional, (123)
"Great location, quiet got a good night sleep. Dusting could be improved but overall pretty clean.. Would stay again"
The price is NZ$519
per night
28 May - 29 May
Unbeatable Downtown Mystic Location
Beach nearby, sun-loungers, beach towels
Beach House
9.8 out of 10, Exceptional, (42)
"This was such a cute place. We visited in spring where everything is just start to bloom the yard was fenced in so great for dogs, with a cute play place for kids. The neighborhood is so quiet and peaceful. We walked several of the streets and meet a few friendly neighbors. The host was fantastic checking in to make sure we had everything we needed. The house was clean, Air with lots of windows and light. We spent time playing board games and reconnect. Definitely would come the area again and...
Beach House
Fridge, microwave, oven, stovetop
Awesome 7 Bedrooms on the Water including 3 More studio cottages by summer 2024
9.8 out of 10, Exceptional, (12)
"Absolutely perfect! Close to so many things to do. House was so group friendly and the host is so accommodating Will be sure to keep this listing in mind to come and stay again."
Awesome 7 Bedrooms on the Water including 3 More studio cottages by summer 2024
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See all available properties in Old Saybrook
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.

Other types of properties in Old Saybrook you may be interested in

Exterior
Saybrook Point Resort & Marina
3.5 star property
9.4 out of 10, Exceptional, (1000)
"Beautiful property. Excellent food, views, staff."
The price is NZ$659
per night
23 May - 24 May
Saybrook Point Resort & Marina
Room, 2 Queen Beds, Non Smoking
Spark by Hilton Mystic Groton
3.0 star property
8.6 out of 10, Excellent, (268)
"This was a great little hotel. Very reasonably priced, bed and pillows were wonderful. Breakfast was ok, bagels and yogurt and coffee. The area was within walking distance to Mystic Village, a cute little village with shops and restaurants and a 10 mins drive from downtown Mystic. Would stay here again!"
The price is NZ$181
per night
28 May - 29 May
Spark by Hilton Mystic Groton
Exterior
Quality Inn Old Saybrook - Westbrook
2.5 star property
7.6 out of 10, Good, (958)
"Staff was very helpful. Check in was easty. Pool was clean. "
The price is NZ$174
per night
22 May - 23 May
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Old Saybrook holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Old Saybrook. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Old Saybrook. Seeing all the best attractions is bound to make you fall in love with Old Saybrook. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Old Saybrook short-term rentals, that won’t be hard to do.

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?

Unbeatable Downtown Mystic Location: This holiday home rental outside Old Saybrook offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

How many holiday rentals will I find in Old Saybrook?

Choose from 58 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.

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