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Fairlee Vacation Rentals

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Check prices for these dates

In two weeks
Nov 6 - Nov 8
In two months
Dec 18 - Dec 20
In three months
Jan 15 - Jan 17
In four months
Feb 12 - Feb 14

Our top choices for Fairlee vacation rentals

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

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 CA $139
CA $222 total
includes taxes & fees
Oct 26 - Oct 27
First Floor Studio Apartment in Historic Chestertown
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

2. 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 CA $257
CA $388 total
includes taxes & fees
Oct 26 - Oct 27
Secluded Cottage in Middle of Chestertown
A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

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 CA $174
CA $414 total
includes taxes & fees
Oct 25 - Oct 26
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

4. 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, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is CA $95
CA $175 total
includes taxes & fees
Oct 28 - Oct 29
Guest Suite for up to 2 in a Victorian on the Chester River
A building with a gabled roof and a circular vent on the roof.

5. 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 CA $280
CA $442 total
includes taxes & fees
Oct 27 - Oct 28
BAYSIDE BUNGALOW
A spacious living area with a dining table, sofa, and a kitchen in the background.

6. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 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 CA $315
CA $495 total
includes taxes & fees
Oct 27 - Oct 28
Newly restored apartment in the heart of Chestertown
A modern exterior with a black door, a metal staircase, and a lantern.

7. Cass-Away Luxury Houseboat

Cass-Away Luxury Houseboat
Grasonville
10.0 out of 10, Exceptional, (109 reviews)
"Wonderful stay. House boat was amazing and hosts helpful and responsive! "
United States
Jamie L.
The price is CA $139
CA $442 total
includes taxes & fees
Oct 27 - Oct 28
Cass-Away Luxury Houseboat
A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

8. 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)
"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 CA $175
CA $215 total
includes taxes & fees
Nov 9 - Nov 10
WATERFRONT, PIER, HOT TUB, FIRE TABLE, KAYAKS, AIR HOCKEY, 1 LEVEL
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

9. Turtle Cove Room

Turtle Cove Room
Kent County
The price is CA $227
CA $281 total
includes taxes & fees
Nov 2 - Nov 3
Turtle Cove Room
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

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 CA $244
CA $303 total
includes taxes & fees
Nov 2 - Nov 3
Beachcomber Suite
A living room with a brown leather sofa, a wooden coffee table, and a ceiling fan.

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 CA $277
CA $402 total
includes taxes & fees
Nov 2 - Nov 3
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A single-story house with a front porch, surrounded by a well-maintained lawn and trees.

12. 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 CA $238
CA $487 total
includes taxes & fees
Oct 27 - Oct 28
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

13. 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 CA $221
CA $595 total
includes taxes & fees
Nov 2 - Nov 3
FLOHOM 14 | Luxury Houseboat with Chesapeake Bay Panoramic Views
A wooden door, a rug, a cabinet, and a lamp.

14. 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 CA $427
CA $674 total
includes taxes & fees
Nov 2 - Nov 3
Wren Retweet- Country Estate in Center of C’Town
A modern kitchen with stainless steel appliances, white cabinetry, and a brick backsplash.

15. 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, (16 reviews)
"very wonderful home and very quite area "
United States
alan d.
The price is CA $279
CA $489 total
includes taxes & fees
Oct 27 - Oct 28
B’more Restful. Comfortable Townhome -Easy access to everywhere
A narrow hallway with a kitchen area on one side, featuring a microwave, oven, and cabinets. There are three black bar stools along the hallway, and a potted plant on the counter.

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 CA $164
CA $539 total
includes taxes & fees
Oct 24 - Oct 25
Abingdon Haven Hideaway
A kitchen with wooden cabinets, a dining table, and a refrigerator.

17. 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.
The price is CA $367
CA $464 total
includes taxes & fees
Nov 1 - Nov 2
Family Retreat at Lansdowne Manor
A wooden dock with Adirondack chairs and a ladder, overlooking a calm body of water with a distant shoreline.

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 CA $504
CA $931 total
includes taxes & fees
Oct 26 - Oct 27
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

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Everyone seemed to care and were nice"
james 1-night trip
Posted 3 hours ago
Hampton Inn & Suites Edgewood/Aberdeen-South

Find out more about Fairlee

Everything you need to know about Fairlee vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Fairlee vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Fairlee vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Fairlee vacation rentals we have selected for you start as low as CA $215 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 vacation 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 vacation.

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 vacation rentals in Fairlee?

Yes, we give you a choice of vacation rentals near top sights in Fairlee, or you can choose a secluded option if you're looking for a relaxing stay.

What's the top vacation rental that Fairlee has to offer?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: Visitors like this Fairlee vacation home rental. It offers a balcony, a garden, and a barbecue grill 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 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 larger area.

What’s a vacation rental in Fairlee like?

Vacation rentals are privately owned properties where you can stay for several days or longer in Fairlee. Vacation rentals feature extras such as kitchens and laundry facilities so you'll have everything you want. If you're concerned about cleanliness, a vacation rental can provide a sense of security away from shared hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular choice for family gatherings.