Holiday rentals in Fairhaven

4.9 out of 5 average rating, 102 reviews

Quiet Coastal Cottage Escape with Water Views

Want to get away? Come relax and escape in our updated bay view cottage. You'll enjoy stunning sunsets, warm surroundings, and all the amenities you could want in our cozy, peaceful cottage home. You'll find plenty of comfortable spots to relax, inside and out. Located on a quiet street, while still close to the small-town charm and offerings of North Beach, Chesapeake Beach, and Herrington Harbor. Walk along the bay, enjoy the local restaurants, and get ready to relax. Stay a week and save!

5 out of 5 average rating, 141 reviews

Home in North Beach

Waterfront, Dog-friendly, Hot Tub, Peleton

A spectacular, spacious 2 bed, 2.5 bath, pet friendly, waterfront home with stunning, unobstructed views located directly on the Chesapeake Bay. Short walk to beach and pier and several bars and restaurants. A large gourmet kitchen provides everything you'lli need. Workout on the in-house Peleton bike & treadmill. Two cruising bikes are yours to explore town or bike to dinner. Enjoy the private hot tub and 2 gas fireplaces. Solo stove on back deck. **Message host for add’l winter dates**

4.96 out of 5 average rating, 156 reviews

Bell Estates I Beautiful Cottage I *Beach Passes*

Bell Estates is a newly built corner lot across the street from the bay with minimal views of the water from Master bedroom and front yard. Located in the heart of North Beach in the exclusive Holland Point neighborhood, our home provides a cozy get-a-way for a family looking to escape the hustle and bustle of life. Home is 2 minutes away from Herrington Harbor, Ketch 22, North Beach Boardwalk & more. Enjoy local accessibility to fishing from the boardwalk dock or rent a boat to go crabbing.

4.94 out of 5 average rating, 163 reviews

Club Carp North Beach - Steps to the Bay!

Calendar open for bookings in April 2025! Welcome to Club Carp North Beach. A charming and cozy cottage just 3 blocks to the Boardwalk/Beach. Renovated throughout with 3 bedrooms and 2 full baths. Perfect place for a relaxing, family vacation! This kid-friendly home has a large fenced side yard with swing set, play area for the kiddos, and lots of extra amenities with families in mind. Comfortable outdoor dining area with fire pit and gas grill. Just steps to restaurants, shopping, and bars.

Guest house in Lyon Village

4.95 out of 5 average rating, 170 reviews

Nautical Charm and relaxing waterview!

Our comfortable and relaxing studio is a quiet retreat with a fantastic view while still in close proximity to Washington DC, Annapolis and Baltimore! Situated in a charming waterfront and sailing community, this separate and private unit has: parking, 1 bath, queen bed, kitchen (limited), TV, high speed WiFi and Bluetooth speaker. Wake up to the cluck cluck of our four resident chickens who are tucked away in their attractive coop. Sit on the porch and take in the view!

4.98 out of 5 average rating, 124 reviews

Home in West River

Cozy waterview home in West River!

Your family will be close to everything when you stay at this centrally-located place. This home is located just 15 miles to Annapolis, 18 miles to the Naval Academy, and 30 miles to the heart of Washington, DC. Less then 8 miles to Rt 214, providing direct access to beltway, and other major highways. This charming home has as spacious fenced in yard, High Speed Internet, TV (Netflix & Hulu), outdoor seating and a fire pit. Want to get away? Bring the whole family!

4.99 out of 5 average rating, 212 reviews

Home in Tracys Landing

The Little Gypsy BoHome

Welcome to our Little Gypsy BoHome on the bay! The house is situated in Southern Anne Arundel County, MD in the quaint waterfront town of Tracy's Landing. Our home sits directly on The Chesapeake Bay with breathtaking views from every window. We offer a saltwater swimming pool, two corn hole game sets, a basketball hoop, beach access, canoe, 2 Paddle Boards, a gas grill, and a steam shower, an outdoor redwood panoramic barrel sauna and a redwood cold plunge!

4.97 out of 5 average rating, 148 reviews

Home in North Beach

Huge Beach Home | 2 King Bds | Backyard Dining

Welcome to Palm Haven at A Haven Away! Our home has 4 bedrooms (2 king beds + 2 queen beds). 2 mins to the beach, restaurants, and wetlands. We have a private, landscaped backyard perfect for dining and lounging. We provide beach passes, beach gear, games, a Pack & Play, and tips for jet ski rentals and day trips. The shed has a huge Smart TV. Fully-equipped kitchen. Single-story living with 2 bedrooms, accessible shower on the ground floor.

4.82 out of 5 average rating, 181 reviews

Cottage in Deale

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Savor our three-bedroom Cottage in this peaceful western shore spot, enjoy two acres of green space, the pier, kayaks, swings, fire pit, shady lawns & sun-drenched loungers, local waterfront dining or eat in, close to Washington, D.C., Annapolis, & Baltimore at this honeymoon-worthy country-like micro-resort. Due to the current COVID-19 situation, we have offered SPECIAL discounts for longer-term rentals

Guest suite in Chesapeake Beach

4.96 out of 5 average rating, 115 reviews

Nice Guest Suite at Chesapeake Bay

Take it easy at this unique and tranquil getaway. Come and relax in our modern & comfortable guest suite to enjoy a small-town quiet setting with amazing Chesapeake Bay views. A short drive from Washington DC (45 min), Annapolis (30 Min), or Baltimore (1 hr). Groceries, boardwalks, restaurants are all within walking distance. Enjoy cable TV, high-speed Internet, and strong wifi through Xfinity.

4.96 out of 5 average rating, 160 reviews

Cottage in Deale

Chesapeake Bay Cottage

Cottage Located directly on the Chesapeake Bay. Includes sandy beach, yard, a screened in porch and deck. Two Kayaks to enjoy. Two bedroom plus den. Two full baths. Fully equipped kitchen.Kurig coffee maker and regular available. Master bedroom -queen size mattress. Second bedroom -a full-size mattress (double) third bedroom -a twin day bed with twin pullout. Both twin size mattresses.

4.97 out of 5 average rating, 329 reviews

Waterfront Cottage Near Herrington and North Beach

Escape to Osprey Cottage, a renovated oasis overlooking the Chesapeake Bay. Our home is a 1930s bungalow that has been tastefully updated with modern sensibility, while still preserving its original charm. Streamlined decor, gleaming wood floors, and stunning views from the common spaces, deck, and hot tub invite you to simply relax.

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Other great holiday rentals in Fairhaven

4.99 out of 5 average rating, 81 reviews

Home in Deale

Herring Bay Getaway Water view | Deale, Maryland

IrisRating, 5 stars2 weeks ago

The place was everything I wanted for my vacation. I will come back for another relaxing weekend. Many thanks to the kind and helpful hosts.

5 out of 5 average rating, 53 reviews

Flat in Davidsonville

Aspen Woods

Gina MichelleRating, 5 stars2 weeks ago

I have nothing but good things to say about Donna and Ken. When we arrived, it was pouring rain. We had a long trailer with us and we needed to park it. Ken already had the doors open for us and helped my husband get the trailer parked in the rain. Then the next morning, he helped my husband get it backed out. The garage apartment was perfect. It was clean and felt like home. I absolutely love their place. It has everything that you need while you are there. It definitely is home away from home. The area that it is in is very nice. They have several nice restaurants. We plan on coming back in the future but without the trailer. Donna and Ken are wonderful host. Thank you so much for loaning your place out for others to enjoy.

Holiday home in Chesapeake Beach

4.98 out of 5 average rating, 65 reviews

Chesapeake Bay Apartment w/Free Season Beach Pass!

PatriciaRating, 5 stars2 weeks ago

This was my third visit (second with my daughter and granddaughter). As always, we felt very comfortable. The Airbnb was spotless and had every amenity we needed to feel right at home. As a bonus, we got to meet Inna during our visit and were impressed with her warmth and hospitality. We really enjoyed the homemade cookies too!

4.87 out of 5 average rating, 95 reviews

Bungalow in North Beach

Bayside Bungalow: Cozy North Beach Getaway

KimberlyRating, 5 stars1 week ago

Perfect getaway spot on North Beach! Location, location, location!! Walkable to boardwalk, pier, great restaurants and shops. Although it is an older home it has been nicely renovated and we especially loved the front porch where we spent our time relaxing in the morning before we headed out for the day. Extremely responsive host! 5 Star Stay! We would not hesitate to book again!

5 out of 5 average rating, 11 reviews

Home in Shady Side

The Wise Quack 2 - A Taste of the Chesapeake Bay!

ToddRating, 5 stars1 week ago

The Wise Quack 2 is a cozy, clean Airbnb steps from the Chesapeake Bay, perfect for a relaxing getaway. Sidco’s warm hospitality, comfy beds, and thoughtful touches like the deep tub and hammock make it a gem. The quiet Shady Side location and quick host responses ensure a delightful stay.

Superhost

Flat in North Beach

4.88 out of 5 average rating, 80 reviews

Spacious Beach House Top Floors - Walk Everywhere!

BeckyRating, 5 stars2 weeks ago

We really enjoyed our stay at Maria’s place! Everything was comfortable, clean, and convenient. The house has character and charm while also being modern with a luxurious feel to it. We walked to and highly recommend the Bakist for coffee and breakfast!

Superhost

Home in North Beach

5 out of 5 average rating, 21 reviews

Harbor Breezes at Herrington

KathleenRating, 5 stars3 weeks ago

Harbor Breeze at Herrington was just lovely and exactly as pictured! We were there to celebrate our son’s wedding weekend and the location is perfect for a wedding at Herrington on the Bay- very close to the venue, the Inn the market, and Ketch 22 where we had our welcome dinner. Tacy was so nice to allow our us an early arrival so we could get ready for the Welcome Dinner🥰We were very happy staying at Harbor Breeze. Due to the busy weekend we did not spend a lot of time at the house but it seemed the house was well stocked with all the essentials you would need. Harbor Breeze is a wonderful place to stay if you are visiting North Beach.