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Fairlee Holiday Rentals

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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Fairlee holiday rentals

Property grounds

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (122 reviews)
"Exactly as advertised. Great room, clean and highly recommended. "
United States
S G.
The price is HK$777
HK$1,246 total
includes taxes & fees
20 Aug - 21 Aug
First Floor Studio Apartment in Historic Chestertown
Beach

2. 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, (28 reviews)
"What a great apartment and location for a getaway. Had everything we needed and so convenient! I will absolutely stay here again."
United States
Charlotte M.
The price is HK$924
HK$2,249 total
includes taxes & fees
20 Aug - 21 Aug
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Smart TV, books

3. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (32 reviews)
"Wonderful spot in the center of historical Chestertown,"
United States
Anonymous traveller
The price is HK$1,765
HK$2,770 total
includes taxes & fees
30 Aug - 31 Aug
Newly restored apartment in the heart of Chestertown
TV, fireplace

4. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is HK$1,440
HK$2,215 total
includes taxes & fees
2 Sept - 3 Sept
Secluded Cottage in Middle of Chestertown
Exterior detail

5. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is HK$1,412
HK$2,269 total
includes taxes & fees
20 Aug - 21 Aug
BAYSIDE BUNGALOW
Property grounds

6. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is HK$2,516
HK$3,925 total
includes taxes & fees
2 Sept - 3 Sept
Wren Retweet- Country Estate in Center of C’Town
Smart TV

7. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is HK$1,804
HK$3,376 total
includes taxes & fees
17 Sept - 18 Sept
Bayside Cottage steps from Rock Hall Harbor
Beach nearby

8. Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (26 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is HK$1,765
HK$2,969 total
includes taxes & fees
30 Aug - 31 Aug
Waterfront Retreat with Private Dock and Beach
1 bedroom, WiFi, bed sheets

9. Turtle Cove Room

Turtle Cove Room
Kent County
The price is HK$1,101
HK$1,367 total
includes taxes & fees
24 Aug - 25 Aug
Turtle Cove Room
Property grounds

10. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...
United States
Lisa E.
The price is HK$1,251
HK$1,547 total
includes taxes & fees
24 Aug - 25 Aug
Beachcomber Suite
Exterior

11. 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
9.8 out of 10, Exceptional, (26 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 HK$533
HK$981 total
includes taxes & fees
10 Sept - 11 Sept
Guest Suite for up to 2 in a Victorian on the Chester River
Property grounds

12. FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Pasadena
10.0 out of 10, Exceptional, (1 review)
"My wife and I had a great time staying in this houseboat. It was our first time ever trying a houseboat and it did not disappoint us at all. The house was very clean and the host provides fully stocked kitchen cabinets, toiletries, towels, etc...We spent most of our time on the rooftop patio, soaking in the sun, and relaxing by the fire pit playing games. The bed was very comfortable as well. It was a great weekend, at a great house that has the benefit of being in a gated marina which was an...
United States
Justin M.
The price is HK$1,293
HK$3,423 total
includes taxes & fees
25 Aug - 26 Aug
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
Terrace/patio

13. WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Aberdeen
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful location, nicely decorated. The host thought of everything you may need including a free snack basket, washer/dryer with detergent and dryer sheets, BBQ grill with utensils, board games and cards, kayaks and life vests, hot tub, firetable etc."
United States
Andy W.
The price is HK$1,600
HK$1,937 total
includes taxes & fees
31 Aug - 1 Sept
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
Dining

14. 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, (16 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 HK$1,961
HK$3,326 total
includes taxes & fees
20 Aug - 21 Aug
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Interior

15. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is HK$2,651
HK$3,225 total
includes taxes & fees
2 Sept - 3 Sept
Family Retreat at Lansdowne Manor
Interior

16. Abingdon Haven Hideaway

Abingdon Haven Hideaway
Abingdon
7.0 out of 10, Good, (2 reviews)
"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 HK$918
HK$3,001 total
includes taxes & fees
29 Aug - 30 Aug
Abingdon Haven Hideaway
Property grounds

17. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (23 reviews)
"Excellent Property"
United States
Buu T.
The price is HK$2,824
HK$5,213 total
includes taxes & fees
20 Aug - 21 Aug
Chesapeake Cottages- 2 Quaint Waterfront Retreats
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

Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina

8/10 Good
"We had a wonderful stay at Hilton Garden Kent Island Marina. This is our second time staying at this hotel and plan to come back next year. Unfortunately, our first night , we were met with a dirty spread and one of the beds had ll inening under the bed draping down."
Dierdre 3-night trip
Posted 5 hours ago
Hilton Garden Inn Kent Island Marina

Find out more about Fairlee

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

  • View our selection of featured holiday rentals in Fairlee
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  • Enter your travel dates to view the best deals on holiday rentals in Fairlee while they last

Look no further and take a look at our great range of rental properties in Fairlee!

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?

Waterfront Oasis w/ Private Dock, Firepit, Arcade & Sunset Views: This holiday home rental outside of Fairlee is located on a river, and has a patio, 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. Make the most of an arcade/games room in this rental home to help you unwind.

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 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.