Fairlee Holiday Rentals from NZ$269: Search Short-Term Rentals

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Our top choices for Fairlee holiday rentals

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

1. First Floor Studio Apartment in Historic Chestertown

Chestertown

S G.

includes taxes & fees

2 Sept - 3 Sept

A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

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

Rock Hall

lisa p.

includes taxes & fees

1 Sept - 2 Sept

3. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

includes taxes & fees

1 Sept - 2 Sept

A building with a gabled roof and a circular vent on the roof.

4. BAYSIDE BUNGALOW

Rock Hall

Diane V.

includes taxes & fees

1 Sept - 2 Sept

A sandy beach with a wooden walkway leading to a calm lake, surrounded by dense green foliage.

5. Waterfront Retreat with Private Dock and Beach

Worton

Max G.

includes taxes & fees

1 Sept - 2 Sept

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

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

Millington

Riley B.

includes taxes & fees

14 Sept - 15 Sept

A spacious living area with a dining table, sofa, and a kitchen in the background.

7. Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveller

includes taxes & fees

1 Sept - 2 Sept

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

Chestertown

includes taxes & fees

8 Sept - 9 Sept

A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

9. Beachcomber Suite

Kent County

"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...

Lisa E.

includes taxes & fees

14 Sept - 15 Sept

A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

10. Turtle Cove Room

Kent County

includes taxes & fees

14 Sept - 15 Sept

A park with a curved wooden bridge, a tree with purple blossoms, and a grassy area.

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

Chestertown

Mandy D.

includes taxes & fees

1 Sept - 2 Sept

A modern exterior with a black door, a metal staircase, and a lantern.

12. Cass-Away Luxury Houseboat

Grasonville

Jamie L.

includes taxes & fees

3 Sept - 4 Sept

A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

13. Bayside Cottage steps from Rock Hall Harbor

Rock Hall

Adam S.

includes taxes & fees

29 Sept - 30 Sept

A fire pit with flames, surrounded by a metal frame, overlooking a body of water with a dock and trees in the background.

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

Aberdeen

includes taxes & fees

1 Sept - 2 Sept

A dining area with a wooden table and chairs, beige curtains, and a ceiling light fixture.

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

Grasonville

Robin

includes taxes & fees

1 Sept - 2 Sept

A view through a window of a wooden deck with a round table and chairs, overlooking a grassy area with trees.

16. Family Retreat at Lansdowne Manor

Centreville

Emily C.

includes taxes & fees

2 Sept - 3 Sept

A sunset view from a balcony with a glass-top table and a fire feature, overlooking the sea.

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

Pasadena

Maria D.

includes taxes & fees

15 Sept - 16 Sept

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.

18. Abingdon Haven Hideaway

Abingdon

Pam L.

includes taxes & fees

5 Sept - 6 Sept

A wooden dock with Adirondack chairs and a ladder, overlooking a calm body of water with a distant shoreline.

19. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Pasadena

Buu T.

includes taxes & fees

1 Sept - 2 Sept

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Top Fairlee Hotel Reviews

Holiday Inn Express White Marsh by IHG

10/10 Excellent

"Great place. Clean friendly. Love the breakfast."

Home2 Suites by Hilton Baltimore/White Marsh

8/10 Good

"There was a person at the front desk that was rude and disrespectful, along with discriminatory about who she helped. The rest of the staff were very welcoming and helpful. I don't know if it was a one time thing, but the first rooms we received were not cleaned and it looked like someone's belongings were still in the other one. The outdoor grill outside of the pool had mice living on it. The outside patio area in front of the hotel were infested with spiders, but they are a part of nature. Despite what I pointed out, the hotel was pretty clean and very cold lol!!!! I will go back to this hotel. I just won't go hang outside. The breakfast was good as well."

The Lodge at Great Oak Landing

10/10 Excellent

"Gem of a local place on the water. The rooms are big and the beds are soooo comfy. The pool is cute and the beach has bands on weekends. There are gas grills and a decent restaurant. It's not fancy (for fancy stay at the manor next door). But it's not corporate either. It's authentic, peaceful and fun."

Fairfield Inn & Suites by Marriott White Marsh

8/10 Good

"My overnight stay was really nice. My room was clean and the room layout was great. The mattress could have been a bit firmer for me, however, I slept like a log! The one issue I mentioned as I checked out of the room was a crack on the shower wall. The associate at the desk said she was not aware of the crack. I am certain they will take care of it. The staff was so attentive. I appreciate the shower cap they provided me with! I will definitely stay here again soon."

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$269 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?

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 Ferry Park. 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.

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Check prices for these dates

Our top choices for Fairlee holiday rentals

1. First Floor Studio Apartment in Historic Chestertown

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

3. Secluded Cottage in Middle of Chestertown

4. BAYSIDE BUNGALOW

5. Waterfront Retreat with Private Dock and Beach

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

7. Newly restored apartment in the heart of Chestertown

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

9. Beachcomber Suite

10. Turtle Cove Room

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

12. Cass-Away Luxury Houseboat

13. Bayside Cottage steps from Rock Hall Harbor

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

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

16. Family Retreat at Lansdowne Manor

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

18. Abingdon Haven Hideaway

19. Chesapeake Cottages- 2 Quaint Waterfront Retreats

Find holiday rentals that suit your style

Top Fairlee Hotel Reviews

Holiday Inn Express White Marsh by IHG

Home2 Suites by Hilton Baltimore/White Marsh

Hampton Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

Hampton Inn & Suites Edgewood/Aberdeen-South

The Lodge at Great Oak Landing

Fairfield Inn & Suites by Marriott White Marsh

Best Western Kent Narrows Inn

The Inn at Chesapeake Bay Beach Club

Find out more about Fairlee

Frequently asked questions

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