Fairlee Holiday Rentals

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Holiday Rentals in Fairlee

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 NZ$501
includes taxes & fees
21 Nov - 22 Nov
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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

Betterton
The price is NZ$740
includes taxes & fees
1 Dec - 2 Dec
Grandma’s Cottage will wrap around you like a warm hug

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 NZ$221
includes taxes & fees
24 Nov - 25 Nov
Guest Suite for up to 2 in a Victorian on the Chester River

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 NZ$740
includes taxes & fees
21 Nov - 22 Nov
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

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 NZ$528
includes taxes & fees
21 Nov - 22 Nov
BAYSIDE BUNGALOW

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (106)
"Amazing and neat and very private "
United States
Alexander M.
The price is NZ$281
includes taxes & fees
25 Nov - 26 Nov
First Floor Studio Apartment in Historic Chestertown

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 NZ$481
includes taxes & fees
21 Nov - 22 Nov
Chesapeake Bay Harbor View in a central location to events/restaurants

High Tide Haven Suite

Kent County
The price is NZ$353
includes taxes & fees
21 Nov - 22 Nov
High Tide Haven Suite

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 NZ$550
includes taxes & fees
23 Nov - 24 Nov
Waterfront Retreat with Private Dock and Beach

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 NZ$793
includes taxes & fees
1 Dec - 2 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit

FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

Pasadena
The price is NZ$872
includes taxes & fees
23 Nov - 24 Nov
FLOHOM 14 Luxury Houseboat with Chesapeake Bay Panoramic Views

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 NZ$540
includes taxes & fees
21 Nov - 22 Nov
Modern and Cozy Home in Bel Air with a Home Office and Fireplace

Sparkling new! A Craftsman-style cottage in the heart of Rock Hall

Rock Hall
10.0 out of 10, Exceptional, (2)
"I spent a wonderful 8 nights at the Dragonfly Cottage in the quaint bayside town of Rock Hall. The cottage was in a prime location and perfectly situated for long morning walks around the town. The cottage itself is brand new with every accommodation you can think of to have a comfortable stay. The 3 large bedrooms and open floor plan kitchen / living area provide plenty of space to spread out. Everything was sparkling clean and you can tell the hosts have taken a lot of care to anticipate your...
United States
Alison F.
The price is NZ$1,021
includes taxes & fees
22 Nov - 23 Nov
Sparkling new! A Craftsman-style cottage in the heart of Rock Hall

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena
9.6 out of 10, Exceptional, (22)
"Excellent Property"
United States
Buu T.
The price is NZ$1,174
includes taxes & fees
24 Nov - 25 Nov
Chesapeake Cottages- 2 Quaint Waterfront Retreats

Abingdon Haven Hideaway

Abingdon
7.0 out of 10, Good, (2)
"We made good use of this rental, it was convenient to all our family & activities. Host is very kind & quickly helpful on request. The main problem with a basement apt is that the thermostat is usually upstairs in the main house, but host was most accommodating about temperature control. We rested well here and had a nice week."
United States
Pam L.
The price is NZ$685
includes taxes & fees
1 Dec - 2 Dec
Abingdon Haven Hideaway

Close to Hospital & White Marsh! Rosedale Townhome

3.0 star property
Nottingham
The price is NZ$883
includes taxes & fees
30 Nov - 1 Dec
Close to Hospital & White Marsh! Rosedale Townhome

Chesapeake Bay Retreat W/Breathtaking Views

Rock Hall
10.0 out of 10, Exceptional, (1)
"Beautiful home situated right on the water with everything we could need. Would not hesitate to return! "
United States
josh b.
The price is NZ$1,424
includes taxes & fees
4 Dec - 5 Dec
Chesapeake Bay Retreat W/Breathtaking Views

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

Edgewood
The price is NZ$774
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

Close to Hospital & White Marsh! Rosedale Townhome

2.0 star property
Nottingham
The price is NZ$942
includes taxes & fees
30 Nov - 1 Dec
Close to Hospital & White Marsh! Rosedale Townhome

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

Cape Saint Claire
10.0 out of 10, Exceptional, (28)
"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 NZ$1,437
includes taxes & fees
2 Dec - 3 Dec
Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly
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 favorite 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 depends 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 NZ$281 per night. Entering your travel dates in the search wizard you might find 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.