Fairlee Holiday Rentals

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Holiday Rentals in Fairlee

Guest Suite for up to 2 in a Victorian on the Chester River

Millington
9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is AU$192
includes taxes & fees
15 Dec - 16 Dec
Guest Suite for up to 2 in a Victorian on the Chester River

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
The price is AU$243
includes taxes & fees
8 Dec - 9 Dec
First Floor Studio Apartment in Historic Chestertown

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Rock Hall
10.0 out of 10, Exceptional, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
The price is AU$446
includes taxes & fees
9 Dec - 10 Dec
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

BAYSIDE BUNGALOW

Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is AU$446
includes taxes & fees
3 Jan - 4 Jan 2026
BAYSIDE BUNGALOW

Waterfront Retreat with Private Dock and Beach

Worton
10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
The price is AU$474
includes taxes & fees
8 Dec - 9 Dec
Waterfront Retreat with Private Dock and Beach

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
The price is AU$413
includes taxes & fees
19 Dec - 20 Dec
Chesapeake Bay Harbor View in a central location to events/restaurants

Enjoyable 4-bedroom house can stay 6. 1 Qn bed is Air Matt. Parking up to 4 cars

Edgewood
10.0 out of 10, Exceptional, (1)
"The home was a good size...Had a good amount of amenities...it was perfect for what my family needed...The ADA accomodations were great for my disabled son...the host was responsive and a answered any questions quickly. "
United States
ROSEMARIE C.
The price is AU$701
includes taxes & fees
7 Dec - 8 Dec
Enjoyable 4-bedroom house can stay 6. 1 Qn bed is Air Matt. Parking up to 4 cars

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is AU$637
includes taxes & fees
19 Dec - 20 Dec
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

HGTV quality, private guest suite, country getaway with hot tub & fire pit

Centreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is AU$681
includes taxes & fees
15 Dec - 16 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit

High Tide Haven Suite

Kent County
The price is AU$304
includes taxes & fees
12 Dec - 13 Dec
High Tide Haven Suite

New! Stylish downtown home w/awesome outdoor area!

Stevensville
9.8 out of 10, Exceptional, (26)
"The house was spacious, clean, and in a great location. The owners were available, and easy to communicate with."
United States
Marjorie N.
The price is AU$814
includes taxes & fees
25 Dec - 26 Dec
New! Stylish downtown home w/awesome outdoor area!

Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly

Cape Saint Claire
10.0 out of 10, Exceptional, (29)
"We only had a short stay but the communication with Justin was extremely quick and responsive - very clear and a great host. The property was really clean, welcoming and perfect for our short break. "
United States
Lee B.
The price is AU$1,266
includes taxes & fees
9 Dec - 10 Dec
Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly

Close to Hospital & White Marsh! Rosedale Townhome

3.0 star property
Nottingham
The price is AU$808
includes taxes & fees
18 Dec - 19 Dec
Close to Hospital & White Marsh! Rosedale Townhome

Close to Hospital & White Marsh! Rosedale Townhome

2.0 star property
Nottingham
The price is AU$803
includes taxes & fees
14 Dec - 15 Dec
Close to Hospital & White Marsh! Rosedale Townhome

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
The price is AU$1,012
includes taxes & fees
8 Dec - 9 Dec
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Bel Air
10.0 out of 10, Exceptional, (5)
"I appreciated how clean and pleasant it smelled! Then it was a beautiful location with lots of places to eat nearby. My only improvement would have been window curtains, especially in the master bath. "
United States
Leah M.
The price is AU$429
includes taxes & fees
5 Jan - 6 Jan 2026
Modern and Cozy Home in Bel Air with a Home Office and Fireplace

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Pasadena
The price is AU$643
includes taxes & fees
18 Dec - 19 Dec
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Luxury Waterfront Home Built for Entertaining!

Abingdon
8.4 out of 10, Very good, (6)
"Quite lovely house with a gorgeous view over the water. It is definitely a good spot to stay with a large family or friends for a few days with plenty to do (relaxing on the dock, play games inside, not too far from Baltimore and other nice towns, etc). The host was great and very communicative as well.The only downsides were details around cleanliness and the check-out procedures. The house itself was overall fine, but there dishes left in the dishwasher that we had to put away, the bottom...
United States
Benjamin J.
The price is AU$1,265
includes taxes & fees
11 Dec - 12 Dec
Luxury Waterfront Home Built for Entertaining!

Grandma’s Cottage will wrap around you like a warm hug

Betterton
The price is AU$634
includes taxes & fees
1 Jan - 2 Jan 2026
Grandma’s Cottage will wrap around you like a warm hug
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 Fairlee Hotel Reviews

Find out more about Fairlee

Everything you need to know about Fairlee holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Fairlee holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Fairlee holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Fairlee holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Fairlee. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Fairlee holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Fairlee holiday rentals we have selected for you start as low as AU$243 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Fairlee rentals

At Expedia, we put the best Fairlee holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Fairlee rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Fairlee holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Fairlee. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Fairlee?

Yes, there are holiday rentals close to the most popular sights in Fairlee, or you can select a more secluded option if you're looking for a relaxing stay.

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

Firepit, Beach, Pier and Gorgeous views without leaving your home ! ! !: This holiday home rental outside of Fairlee is located on the beach, and has a fireplace, a patio and air conditioning to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

What’s there to see and do in Fairlee?

Explore the area and family-friendly sights such as Hazel Miner Monument, or get out into nature at a spot like Betterton Beach. Washington College and Chestertown Historic District are a couple of places you'll find in the wider area.

What’s a holiday rental in Fairlee like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Fairlee. Holiday rentals offer extras like laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from shared 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 traditional hotel, which makes a holiday rental a popular option for family gatherings.