Fairlee Vacation Rentals

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Check prices for these dates

In two weeks
Sep 12 - Sep 14
In one month
Sep 26 - Sep 28
In two months
Oct 24 - Oct 26
In three months
Nov 21 - Nov 23

Vacation Rentals in Fairlee

Our top choices for Fairlee vacation rentals

Cass-N-Reel Luxury Houseboat
Marina

Cass-N-Reel Luxury Houseboat

10.0 out of 10, Exceptional, (37)
"We really enjoyed our stay. Looking forward to staying again!"
The price is ￥14,556
￥39,898 total
includes taxes & fees
Sep 1 - Sep 2
Cass-N-Reel Luxury Houseboat
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (32)
"We had 14 family members join us to celebrate my son’s graduation from the Naval Academy. The house is clean, the rooms were great, the property was beautiful, and it was close to USNA. Our family loved the open concept. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
The Heron's Nest at Atlantic Marina
Exterior

The Heron's Nest at Atlantic Marina

9.8 out of 10, Exceptional, (302)
"Nice weekend getaway!"
The Heron's Nest at Atlantic Marina
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
Marina

Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat

9.8 out of 10, Exceptional, (63)
"Awesome place!"
Osprey's Landing at Atlantic Marinas - relaxing waterfront coastal retreat
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (99)
"A charming studio in a quiet neighborhood. great directions from host on how to use the property - "
The price is ￥14,556
￥23,354 total
includes taxes & fees
Sep 1 - Sep 2
First Floor Studio Apartment in Historic Chestertown
Waterfront Oasis w/ Private Dock, 3BR/2BA
Marina

Waterfront Oasis w/ Private Dock, 3BR/2BA

9.4 out of 10, Exceptional, (35)
"Was a good time. Great location Beautiful sunset across the water. Thanks Jeremy "
Waterfront Oasis w/ Private Dock, 3BR/2BA
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Outdoor dining

240' Private Beachfront @Kent Island Love Point - Great for Large Groups

10.0 out of 10, Exceptional, (190)
"We all had wonderful stay at Love point! "
240' Private Beachfront @Kent Island Love Point - Great for Large Groups
Luxury Waterfront Executive Family Home Annapolis with All Amenities
Outdoor dining

Luxury Waterfront Executive Family Home Annapolis with All Amenities

10.0 out of 10, Exceptional, (2)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities
BAYSIDE BUNGALOW
Outdoor dining

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (46)
"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "
The price is ￥29,406
￥44,574 total
includes taxes & fees
Sep 1 - Sep 2
BAYSIDE BUNGALOW
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
Indoor pool

Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach

10.0 out of 10, Exceptional, (10)
Secluded Waterfront Retreat 2 bed 1 1/2 baths private guest house w Pool & Beach
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Beach

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

10.0 out of 10, Exceptional, (12)
"A very well maintained and comfy apartment that is just a short walk to the heart of Rock Hall. My family especially enjoyed the large private backyard. Rick made sure we had everything we needed."
The price is ￥18,232
￥43,489 total
includes taxes & fees
Sep 2 - Sep 3
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
River Front, Private Single Family Home
Property grounds

River Front, Private Single Family Home

10.0 out of 10, Exceptional, (18)
"Host was very helpful and accommodating. Place was adorable with beautiful views, just as depicted. Had everything we needed and more! "
River Front, Private Single Family Home
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Property grounds

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (73)
"House was in a great location and very well appointed. We had everything we needed. Would highly recommend."
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Smart TV, books

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

9.8 out of 10, Exceptional, (54)
"Lovely cottage, well-equipped, immaculately clean. "
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
Historic Downtown Garden Oasis with Private Patio
Property grounds

Historic Downtown Garden Oasis with Private Patio

10.0 out of 10, Exceptional, (37)
"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "
Historic Downtown Garden Oasis with Private Patio
Entire Townhouse in Rock Hall
Exterior

Entire Townhouse in Rock Hall

10.0 out of 10, Exceptional, (30)
"Exactly what we expected. What wasn’t expected is how quiet and serene that entire town is. "
Entire Townhouse in Rock Hall
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Beach nearby, sun loungers, beach towels

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (42)
"This is a jewel as it is private, peaceful with lovely setting."
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Serene Waterfront Cottage with dock and gorgeous views.
Fridge, microwave, dishwasher, coffee/tea maker

Serene Waterfront Cottage with dock and gorgeous views.

9.6 out of 10, Exceptional, (38)
"Nice place with everything I could want. Would stay there again!"
Serene Waterfront Cottage with dock and gorgeous views.
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Fridge, microwave, oven, stovetop

Secluded Waterfront Cottage on 200 acre farm near Queenstown

10.0 out of 10, Exceptional, (103)
"Secluded"
Secluded Waterfront Cottage on 200 acre farm near Queenstown
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Thanksgiving!
Exterior

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Thanksgiving!

10.0 out of 10, Exceptional, (93)
"We stay at Firefly every time we go to visit our son and his family. It works perfectly for us…an oasis for us, and a fun place for the kids to visit, too. Pat and Ken have been the perfect hosts!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, Thanksgiving!
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

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

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 Hazel Miner Monument, or get out into nature at a spot like Ferry Park. 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.