Old Saybrook Vacation Rentals

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Check prices for these dates

In two weeks
Dec 26 - Dec 28
In two months
Feb 6 - Feb 8
In three months
Mar 6 - Mar 8
In four months
Apr 3 - Apr 5

Vacation Rentals in Old Saybrook

Exterior
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy

Cabin in East Haddam

2.0 star property
9.6 out of 10, Exceptional, (88)
"Clean and good service."
United States
Simge
The price is ￥18,484
￥28,402 total
includes taxes & fees
Dec 9 - Dec 10
Postcard Cabins Machimoodus, Outdoor Collection by Marriott Bonvoy
Beach nearby
Cliffside Resort Condominiums

Aparthotel in Greenport

3.0 star property
9.0 out of 10, Wonderful, (249)
"Great stay - beautiful place"
United States
Rebecca
Cliffside Resort Condominiums
Private kitchen
Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages

Vacation Home in Wequetequock

10.0 out of 10, Exceptional, (2)
"Waterfront location by a marina was beautiful. The place is welcoming with a bright, cozy living area. Rooms were clean and spacious, bathrooms modern, kitchen, grill, and deck to enjoy. Had a great experience overall."
United States
Peter L.
Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages
Honeymoon Apartment, 3 Bedrooms, Kitchen | In-room dining
Luxury Furnished Apartments by Hyatus Downtown at Yale

Aparthotel in The Hill

3.5 star property
9.6 out of 10, Exceptional, (60)
"Loved our stay here. "
United States
Christina
Luxury Furnished Apartments by Hyatus Downtown at Yale
Dining
The Mystic Harbor House · walk downtown Mystic · train · aquarium

Vacation Home in Stonington

9.6 out of 10, Exceptional, (8)
"Great house in a fantastic location. Very clean and well supplied. We would definitely stay here again."
United States
David C.
The price is ￥18,017
￥55,548 total
includes taxes & fees
Jan 6 - Jan 7, 2026
The Mystic Harbor House · walk downtown Mystic · train · aquarium
Outdoor dining
Lakeside cottage overhanging the water, beautiful window views across the lake

Cottage in Ledyard

9.8 out of 10, Exceptional, (217)
"Very comfortable, easy to get to and had everything you could need in a house rental! "
United States
Anna K.
The price is ￥12,302
￥33,797 total
includes taxes & fees
Dec 10 - Dec 11
Lakeside cottage overhanging the water, beautiful window views across the lake
1 bedroom, WiFi, bed sheets
Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath

Apartment in New London

10.0 out of 10, Exceptional, (7)
"We had a good experience staying with host, William. Going in and out of our unit was easy with the codes provided. The croissants provided for breakfast were large and delicious. We would stay there again."
United States
Ronald H.
The price is ￥13,669
￥18,826 total
includes taxes & fees
Dec 9 - Dec 10
Cozy spacious bedroom with queen bed, only half mile to Rt.95, exclusive bath
Property grounds
Thames River Retreat · CT College+Casinos+USCGA

Vacation Home in Waterford

10.0 out of 10, Exceptional, (17)
"We stayed at the Thames River House after our wedding with friends and it was the perfect spot. The home was beautiful, very clean, and had everything we needed for a relaxing and memorable stay. Couldn’t have asked for a better experience!"
United States
Brandon W.
The price is ￥33,031
￥94,840 total
includes taxes & fees
Dec 15 - Dec 16
Thames River Retreat · CT College+Casinos+USCGA
Interior
Rustic Lakeside Cabin at White Gate Farm

Cabin in East Lyme

10.0 out of 10, Exceptional, (123)
"5-star lake view. Amazing stay. we absolutely enjoyed visiting this farm every year. "
United States
Mariya S.
Rustic Lakeside Cabin at White Gate Farm
1 bedroom, WiFi, bed sheets
Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in

Apartment in New London

9.6 out of 10, Exceptional, (12)
"William was very thorough with our check in and a pleasure to deal with"
United States
Catherine
The price is ￥13,669
￥18,826 total
includes taxes & fees
Dec 9 - Dec 10
Clean room w/ Queen bed/exclusive bathroom. Free Wifi free parking self check in
Smart TV, video games, books, stereo
Charming Historic House in Downtown Mystic

Vacation Home in Mystic

10.0 out of 10, Exceptional, (161)
"Great house & location!"
United States
Jane D.
The price is ￥26,561
￥54,466 total
includes taxes & fees
Dec 9 - Dec 10
Charming Historic House in Downtown Mystic
Outdoor pool, a heated pool
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise

Condo in Norwich

10.0 out of 10, Exceptional, (40)
"Everything was easy .. comfortable host was very helpful and communicable. "
United States
Cathleen S.
The price is ￥18,873
￥39,451 total
includes taxes & fees
Dec 11 - Dec 12
Cozy Villa Spa Retreat - Near Mohegan, Hot Tub, Pools, Sauna, Spa on Premise
Exterior
Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.

Vacation Home in Stonington

10.0 out of 10, Exceptional, (56)
"The house is adorable and so nicely appointed. It was a perfect location for a quick walk to downtown or to the Museum. Chris is a fabulous host and so accommodating. We would definitely stay again!"
United States
Lynn T.
The price is ￥48,929
￥100,343 total
includes taxes & fees
Dec 9 - Dec 10
Beautifully Restored 1890’s House in beautiful downtown Mystic. 2 bed & 2 baths.
Exterior
Carrick Landing-#4 · walk Mystic-Train/EV Lvl-2 · aquarium

Apartment in Stonington

10.0 out of 10, Exceptional, (2)
"Clean, brand new, very easy. The sleep sofa was even comfortable!"
United States
Maria S.
The price is ￥12,012
￥33,253 total
includes taxes & fees
Dec 9 - Dec 10
Carrick Landing-#4 · walk Mystic-Train/EV Lvl-2 · aquarium
Beach nearby
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA

Vacation Home in New London

8.0 out of 10, Very Good, (16)
"Easy access. We loved our short stay. I would return again. "
United States
Suzanne M.
The price is ￥9,087
￥29,455 total
includes taxes & fees
Dec 15 - Dec 16
Cozy 2-bedroom vacation home《 free WiFi & parking 》New London, Connecticut, USA
Terrace/patio
Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!

Apartment in Westerly

9.4 out of 10, Exceptional, (11)
"It was sweet, small but roomy for 2.A C was wonderful in the hot day. All provisions served us well. "
United States
Mary Alice B.
The price is ￥11,650
￥19,292 total
includes taxes & fees
Dec 21 - Dec 22
Adorable in-law studio w/private entrance-Minutes to downtown, 5 miles to beach!
Private kitchen
Your Charming 4BR Retreat Home Minutes from Casino Excitement!

Vacation Home in Norwich

9.8 out of 10, Exceptional, (11)
"Had a wonderful weekend"
United States
Hector H.
The price is ￥83,738
￥151,147 total
includes taxes & fees
Dec 9 - Dec 10
Your Charming 4BR Retreat Home Minutes from Casino Excitement!
Property grounds
Oak Grove Cottage - in the foothills of Mystic

Vacation Home in Groton

10.0 out of 10, Exceptional, (15)
"Everything was as expected—recommend this location for easy access to Mystic!"
United States
Patrick K.
The price is ￥41,465
￥68,693 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Oak Grove Cottage - in the foothills of Mystic
Dining
Spacious 7-bedroom house Stonington with amazing views.

Vacation Home in Stonington

10.0 out of 10, Exceptional, (5)
"Great place, great owner!"
United States
Harrison M.
Spacious 7-bedroom house Stonington with amazing views.
Fridge, microwave, oven, stovetop
Cozy Coastal Cottage New London

Apartment in New London

9.4 out of 10, Exceptional, (10)
"It was the perfect little place for a night away from the kids. "
United States
Tonya B.
The price is ￥29,823
￥68,581 total
includes taxes & fees
Dec 9 - Dec 10
Cozy Coastal Cottage New London
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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Top Old Saybrook Hotel Reviews

Spark by Hilton Mystic Groton

Spark by Hilton Mystic Groton

10/10 Excellent
"Breakfast was great. Room was clean. Staff was very friendly "
Paula 1-night trip
Posted 2 days ago
Spark by Hilton Mystic Groton

Find out more about Old Saybrook

Search for holiday rentals in Old Saybrook on Expedia! You can easily find your home rentals, villas, holiday apartments in Old Saybrook using one of the methods below:

  • View our selection of featured holiday rentals in Old Saybrook
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Look no further and take a look at our great range of rental properties in Old Saybrook!

Frequently asked questions

Can I find a vacation rental in Old Saybrook?

Yes, there are vacation rentals in Old Saybrook close to Stay and Play LLC, or you can go with a more remote 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 vacation home rentals in Old Saybrook?

Amazing 10 Bedroom Compound on the Water with 6 Bedroom Home & 4 Studio Cottages: This vacation home rental outside of Old Saybrook has air-conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

How many vacation rentals will I find in Old Saybrook?

Choose from 54 Expedia vacation rentals in Old Saybrook for a memorable vacation.

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

Family-friendly attractions include Stay and Play LLC and Saybrook Country Barn, 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 vacation rental in Old Saybrook like?

Vacation rentals are private properties you can stay in for a few weeks or just a few days in Old Saybrook. Vacation rentals offer extras like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about a sanitized environment, vacation rentals can offer a sense of security away from public hotel elevators and busy lobbies while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for family trips.