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Fairlee Holiday Rentals

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Our top choices for Fairlee holiday rentals

1. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is NZ$284
includes taxes & fees
19 Oct - 20 Oct
First Floor Studio Apartment in Historic Chestertown

2. 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, (29 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$223
includes taxes & fees
20 Oct - 21 Oct
Guest Suite for up to 2 in a Victorian on the Chester River

3. 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, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is NZ$503
includes taxes & fees
17 Oct - 18 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

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 NZ$488
includes taxes & fees
27 Oct - 28 Oct
Secluded Cottage in Middle of Chestertown

5. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (33 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is NZ$616
includes taxes & fees
18 Oct - 19 Oct
Newly restored apartment in the heart of Chestertown

6. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is NZ$540
includes taxes & fees
28 Oct - 29 Oct
BAYSIDE BUNGALOW

7. Turtle Cove Room

Turtle Cove Room
Kent County
The price is NZ$353
includes taxes & fees
19 Oct - 20 Oct
Turtle Cove Room

8. 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 NZ$377
includes taxes & fees
19 Oct - 20 Oct
Beachcomber Suite

9. 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 NZ$844
includes taxes & fees
27 Oct - 28 Oct
Wren Retweet- Country Estate in Center of C’Town

10. 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, (11 reviews)
"The host was incredibly friendly and communicative. The place was a lot bigger than I expected, and it was beautiful to sit out by the fire pit and look at the river nearby. And, she left us snacks and smores for the stay! A nice quiet spot to spend a night."
United States
Matthew
The price is NZ$274
includes taxes & fees
4 Nov - 5 Nov
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL

11. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is NZ$548
includes taxes & fees
22 Oct - 23 Oct
Cozy 1-bedroom in-law suite in lovely Chestertown with AC

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, (2 reviews)
"FLOHOM 14 did not disappoint!!! This was my first stay on a houseboat. Now I know why babies fall asleep when rocked. The boat is beautifully appointed & well equipped. Bring a good book. I’m already missing it!!!"
United States
Maria D.
The price is NZ$831
includes taxes & fees
22 Oct - 23 Oct
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views

13. Private 2 story waterfront entire home w/ dedicated pier located on Sue Creek!

Private 2 story waterfront entire home w/ dedicated pier located on Sue Creek!
Essex
The price is NZ$981
includes taxes & fees
16 Oct - 17 Oct
Private 2 story waterfront entire home w/ dedicated pier located on Sue Creek!

14. B’more Restful. Comfortable Townhome -Easy access to everywhere

B’more Restful. Comfortable Townhome -Easy access to everywhere
Dundalk
10.0 out of 10, Exceptional, (15 reviews)
"very wonderful home and very quite area "
United States
alan d.
The price is NZ$609
includes taxes & fees
18 Oct - 19 Oct
B’more Restful. Comfortable Townhome -Easy access to everywhere

15. Welcome to the secluded waterfront oasis

Welcome to the secluded waterfront oasis
Millington
8.0 out of 10, Very good, (3 reviews)
"We really enjoyed our stay here! The house was clean, cozy, and had everything we needed. The host was so nice and easy to communicate with, which made everything really easy. We felt right at home and would definitely stay here again!"
United States
Destiny H.
Welcome to the secluded waterfront oasis

16. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (13 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.
Family Retreat at Lansdowne Manor

17. 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 NZ$657
includes taxes & fees
17 Oct - 18 Oct
Abingdon Haven Hideaway

18. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Chesapeake Cottages- 2 Quaint Waterfront Retreats
Pasadena
9.6 out of 10, Exceptional, (24 reviews)
"Excellent Property"
United States
Buu T.
The price is NZ$1,142
includes taxes & fees
19 Oct - 20 Oct
Chesapeake Cottages- 2 Quaint Waterfront Retreats

19. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
The price is NZ$610
includes taxes & fees
27 Oct - 28 Oct
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Fairlee holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Fairlee. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Fairlee. Seeing all the best attractions is bound to make you fall in love with Fairlee. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Fairlee short-term rentals, that won’t be hard to do.

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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This holiday home rental outside of Fairlee offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 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 Betterton Beach. 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.