Fairlee Holiday Rentals

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Our top choices for Fairlee holiday rentals

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

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.6 out of 10, Exceptional, (23 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is NZ$209
includes taxes & fees
1 June - 2 June
Guest Suite for up to 2 in a Victorian on the Chester River

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (111 reviews)
"Every thing was great"
United States
lesia k.
The price is NZ$265
includes taxes & fees
1 June - 2 June
First Floor Studio Apartment in Historic Chestertown

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (55 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is NZ$497
includes taxes & fees
1 June - 2 June
BAYSIDE BUNGALOW

2 Mi to Apg: Edgewood Family Home w/ Fenced Yard

2 Mi to Apg: Edgewood Family Home w/ Fenced Yard
3.0 star property
Edgewood
The price is NZ$794
includes taxes & fees
25 June - 26 June
2 Mi to Apg: Edgewood Family Home w/ Fenced Yard

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
9.8 out of 10, Exceptional, (28 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is NZ$636
includes taxes & fees
3 June - 4 June
Newly restored apartment in the heart of Chestertown

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

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Grasonville
9.6 out of 10, Exceptional, (13 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is NZ$694
includes taxes & fees
2 June - 3 June
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (22 reviews)
"Excellent Property"
United States
Buu T.
The price is NZ$1,097
includes taxes & fees
1 June - 2 June
Chesapeake Cottages- 2 Quaint Waterfront Retreats

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
The price is NZ$725
includes taxes & fees
2 June - 3 June
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

Turtle Cove Room

Turtle Cove Room
Kent County
The price is NZ$353
includes taxes & fees
4 June - 5 June
Turtle Cove Room

Beachcomber Suite

Beachcomber Suite
Kent County
The price is NZ$301
includes taxes & fees
1 June - 2 June
Beachcomber Suite

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is NZ$629
includes taxes & fees
15 June - 16 June
Waterfront Retreat with Private Dock and Beach

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

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (21 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is NZ$477
includes taxes & fees
1 June - 2 June
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
The price is NZ$604
includes taxes & fees
15 June - 16 June
Bayside Cottage steps from Rock Hall Harbor

Gorgeous 3-bedroom townhome with AC in friendly Dundalk

Gorgeous 3-bedroom townhome with AC in friendly Dundalk
Dundalk
4.0 out of 10, (1 review)
"I think we were the first people to stay at this property. It was a little risky because there wasn’t any reviews yet, but you get what you paid for. It lacked a lot of basic necessities. It was not ready for guests, there were no towels, toilet paper, napkins, etc. One of the beds was missing a blanket, there was a full load of dirty laundry in the washer. The first shower had a body wash and a kids detangle shampoo and the second shower had nothing, so be prepared for that. (Despite the fact...
United States
Anastasia S.
The price is NZ$342
includes taxes & fees
1 June - 2 June
Gorgeous 3-bedroom townhome with AC in friendly Dundalk

The Sparrows Nest - in downtown Sparrows Point

The Sparrows Nest - in downtown Sparrows Point
Edgemere
The price is NZ$402
includes taxes & fees
7 June - 8 June
The Sparrows Nest - in downtown Sparrows Point

2 Mi to APG: Edgewood Family Home w/ Fenced Yard

2 Mi to APG: Edgewood Family Home w/ Fenced Yard
Edgewood
4.0 out of 10, (1 review)
"The house was okay. Definitely wasnt cleaned thoroughly as there was still food stains in the fridge and peices of food in the butter tray inside the fridge. The stove would not work until i set the time to the correct time so that was a bit of a question mark as to why that was. There was ants all over inside the house which personally was very disgusting. Both me and my son woke up with ants crawling on us in both the master bedroom and back bedroom. So that is something that should be...
United States
Sean G.
The price is NZ$769
includes taxes & fees
25 June - 26 June
2 Mi to APG: Edgewood Family Home w/ Fenced Yard

Luxury Waterfront Home Built for Entertaining!

Luxury Waterfront Home Built for Entertaining!
Abingdon
9.0 out of 10, Wonderful, (10 reviews)
"Very clean, spacious and quiet!!!!! Beautiful home! "
United States
Jennifer M.
The price is NZ$1,959
includes taxes & fees
7 June - 8 June
Luxury Waterfront Home Built for Entertaining!
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$342 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?

NEW! Charming Farm House in Historic Kent Island : This holiday home rental outside of Fairlee is located on a river, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

What’s there to see and do in Fairlee?

Explore the area and family-friendly sights such as Crumpton Auction, or get out into nature at a spot like Taylor Island. Washington College and River Arts Chestertown 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.