Waldoboro vacation rentals

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Top-rated vacation rentals in Waldoboro

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Guest favorite

Guest suite in Thomaston

4.86 out of 5 average rating, 111 reviews

Private Top Floor Waterfront Apartment

Welcome to Gabriel's Anchor! 10 min walk to Main St, 10 min drive to Rockland, 2 min walk to public overlook, across the street from the lively Slipway Restaurant, on the waterfront. Gabriel's Anchor is great for couples, families, and solo adventurers looking to stay in the heart of the wonderful coastal Thomaston, Maine. 2 bdrm/1bath. 1 king bed & 1 double. kitchenette has a stovetop, fridge (no freezer, but feel free to use ours if needed), cooking utensils, dishes, coffee maker & coffee.

May 14 – 21

G$19,338 GYD per night

Guest favorite

Apartment in Nobleboro

4.89 out of 5 average rating, 137 reviews

Finding Joy

This lovely apartment is above our garage. You can come and go as you please. We have created a place for peace and solitude. Sit on the deck or look out the dining room window and see the woods and wait for the birds and wildlife that may be wonder through the yard. There is coffee and tea available, along with basic breakfast supplies, if you wish. Keyless entry allows for you to come anytime after check-in. Please note, you have to be comfortable with stairs to access the apartment.

Aug 30 – Sep 6

G$24,190 GYD per night

Guest favorite

Apartment in Damariscotta

4.94 out of 5 average rating, 339 reviews

Cottrill House on Damariscotta River # 1

Cottrell House/Studio. Enjoy the mid-coast in down town Damariscotta Maine. Private entrance, off street parking, private bath, living room with mini fridge, microwave and coffee maker. Private back yard with views over the Damariscotta River. Walk to unique restaurants and shops. Rent a kayak or a paddle board right across the street and enjoy the beautiful views of the Damariscotta River. Only, 25 minutes away from Pemaquid Point and Beach. This is non smoking property!

Apr 10 – 17

G$22,065 GYD per night

Guest favorite

Home in Appleton

4.96 out of 5 average rating, 123 reviews

The Barn

I call my place "The Barn" because as I was finishing it it took the shape and feel of a barn. It's not a barn. It's a quiet post and beam open concept building (a Jamaica Cottages kit) set among the fields of Appleton Maine. You'll sleep in the loft or on a futon on the main floor. The bathroom is huge, 10X10, with a heated floor. It's an open concept kitchen and living space. From Appleton you are 20 miles away from the tourist destinations of Camden, Rockland, and Belfast.

May 4 – 11

G$29,668 GYD per night

Guest favorite

Guesthouse in Rockland

4.88 out of 5 average rating, 315 reviews

Sweet Willow Suite, Rockland, private 1st floor

1-bdrm apartment in stand alone building. Light-filled open area, queen bed, full bath with walk-in shower. Located on a quiet street 1.5 blocks from Main St., restaurants & pubs, thriving arts community, and bus and ferry terminals. Suite includes many safety features. Host is hands-on, will greet you at check-in, then respect your privacy. If you are looking for a totally anonymous experience, this is not it. Licensed with the City of Rockland #STR24-7.

May 18 – 25

G$22,854 GYD per night

Guest favorite

Guest suite in Damariscotta

4.93 out of 5 average rating, 149 reviews

Cozy Carriage House in Downtown Damariscotta

Welcome to Damariscotta, Maine! Our carriage house apartment has the rustic, romantic feel of a classic Maine cabin, but is located a short walk from downtown Damariscotta. Guests have a private studio that includes sleeping accommodations, a bathroom, a small kitchen area, and closet space. This is the perfect spot for adventurous travelers who want to explore the Midcoast of Maine like a local or for creative folks to unplug and focus on their craft.

Sep 4 – 11

G$23,117 GYD per night

Guest favorite

Guest suite in Rockland

4.96 out of 5 average rating, 157 reviews

Salty Dog Hilltop Guest Suite (permit #SDR22-18)

This guest suite is located in the lower level of our NetZero post & beam home which sits on a mountain overlooking the Penobscot Bay. The over 600 sq. ft. large open floor plan is spacious & clean with a large private patio. The location is quiet and peaceful while only 5 minutes from the action in downtown Rockland and only 15 minutes from Camden. This is a great home base to explore all that the Midcoast area has to offer.

Nov 9 – 16

G$31,473 GYD per night

Guest favorite

Guest suite in Rockland

4.98 out of 5 average rating, 347 reviews

5 Laurel Studio private entrance STR20-69

Open concept small studio, private patio and entrance, full kitchen. 2 minute walk to the ocean , Lobster and Blues Festivals. A small swimming beach is a 5 minute walK, 5-10 minutes gets you to the Farnsworth and CMCA museums, Strand Theater, restaurants, antiques shops & galleries. ALSO NOTE we do not have television. We have wifi but you must bring your own device . EXEMPT FROM ACCEPTING SERVICE DOGS

Oct 7 – 14

G$20,489 GYD per night

Guest favorite

Apartment in Damariscotta

4.92 out of 5 average rating, 254 reviews

Fernald's Backside

Fernald's Backside is a sunny, comfortable 2nd floor apartment , tucked behind S. Fernald's Country Store in the heart of downtown Damariscotta. It features a deck with views of the Damariscotta River and Harbor. A one bedroom apartment with ample living space and full kitchen, it can sleep 5 with a double and single bed and a sleeper sofa. Fernald's Backside is Pet free.

Aug 30 – Sep 6

G$31,123 GYD per night

Guest favorite

Cabin in Nobleboro

4.94 out of 5 average rating, 108 reviews

Waterside Cabin the Woods 50 acres-No hidden fees!

Enjoy Maine cottage living the way it used to be! Our 100+ year old cabin is 20'x20' with a kitchen ell and 8'x20' enclosed porch with deck. Kitchen with gas stove, sink. fresh spring water. Gas lighting, no electricity, linens included. Outdoor shower with hot water. Composting toilet. Dock, canoes, paddleboat. Very private setting yet just 10 minutes to Damariscotta.

Apr 21 – 28

G$31,476 GYD per night

Guest favorite

Cabin in Camden

4.83 out of 5 average rating, 708 reviews

Cozy Village Cottage

Cozy, isolated, well stocked cottage cleaned by a professional cleaning crew awaits your visit. Need a quiet, inexpensive 'get away' where you can work and relax? Contact for long term stays this winter and alternatives to the week long requirement.

Feb 25 – Mar 4

G$18,844 GYD per night

Guest favorite

Cabin in Bremen

4.95 out of 5 average rating, 173 reviews

Ocean Front Cottage: Little Heaven

You can't get any closer to the coast of Maine. The cottage perches on a dock next to a small cove. Low tide beach, high tide swimming area, and lapping waves on a near by ledge make this get away a perfect retreat for one or two guests.

Sep 30 – Oct 7

G$33,043 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Waldoboro vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Waldoboro's top sights

Moody's Diner37 locals recommend

Beth's Farm Market25 locals recommend

Bullwinkle's Steak House5 locals recommend

Morse's Sauerkraut30 locals recommend

Delano Seafood Market6 locals recommend

Odd Alewives Farm Brewery22 locals recommend

Other great vacation rentals in Waldoboro

Guest favorite

Guesthouse in South Bristol

4.98 out of 5 average rating, 345 reviews

Waterfront Guest House on the Maine Coast

Jan 15 – 22

G$32,220 GYD per night

Guest favorite

Apartment in Boothbay

4.96 out of 5 average rating, 259 reviews

Sunnymeade

Sep 23 – 30

G$21,254 GYD per night

Guest favorite

Cottage in Saint George

4.96 out of 5 average rating, 188 reviews

Hidden Haven A Rustic Retreat In St. George, Maine

Feb 14 – 21

G$29,887 GYD per night

Guest favorite

Place to stay in Owls Head

4.98 out of 5 average rating, 162 reviews

A comforting sweet off grid cabin near the beach!

Nov 19 – 26

G$30,006 GYD per night

Guest favorite

Cottage in Owls Head

4.99 out of 5 average rating, 139 reviews

Coastal Maine contemporary cottage

Apr 4 – 11

G$28,854 GYD per night

Guest favorite

Guesthouse in Orland

4.99 out of 5 average rating, 103 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Nov 26 – Dec 3

G$21,486 GYD per night

Guest favorite

Home in Lisbon

4.94 out of 5 average rating, 332 reviews

Unplug at a Beachy Bolthole with Classic New England Style

Dec 19 – 26

G$13,798 GYD per night

Guest favorite

Apartment in Edgecomb

4.91 out of 5 average rating, 298 reviews

Sunny Apt in Woods 10 Min to 3 Towns- Dog Friendly

Mar 1 – 8

G$21,810 GYD per night

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Other great vacation rentals in Waldoboro

Guest favorite

Guest suite in Round Pond

4.79 out of 5 average rating, 107 reviews

Round Pond Crows Nest Brand new and ready for you!

Nov 4 – 11

G$19,427 GYD per night

Guest favorite

Home in Waldoboro

4.98 out of 5 average rating, 63 reviews

1830s Cape hosted by George & Paul

Nov 19 – 26

G$20,521 GYD per night

Guest favorite

Apartment in Waldoboro

4.97 out of 5 average rating, 86 reviews

Studio Apartment with Kitchen

Sep 7 – 14

G$21,098 GYD per night

Guest favorite

Home in Waldoboro

5.0 out of 5 average rating, 47 reviews

Small But Mighty (Elegant) Rural Retreat

Jun 23 – 30

G$29,477 GYD per night

Guest favorite

Cabin in Waldoboro

4.95 out of 5 average rating, 19 reviews

Country View Cottage

Oct 23 – 30

G$32,413 GYD per night

Guest favorite

Farm stay in Waldoboro

4.92 out of 5 average rating, 12 reviews

Island View Farm

Feb 12 – 19

G$17,901 GYD per night

Guest favorite

Vacation home in Waldoboro

5.0 out of 5 average rating, 18 reviews

Oceanfront One Bedroom Apartment & Private Deck

Sep 5 – 12

G$37,013 GYD per night

Guest favorite

Guesthouse in Damariscotta

4.95 out of 5 average rating, 21 reviews

The Midcoast Forest Retreat

Dec 4 – 11

G$18,054 GYD per night

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Quick stats about vacation rentals in Waldoboro

Total rentals
80 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
40 properties are a good fit for families
Total number of reviews
2.6K reviews
Nightly prices starting at
G$10,424 GYD before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Waldoboro?
Yes! Work meets play with ease at over 30 vacation rentals in Waldoboro featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Waldoboro?
Four-legged friends are welcome in Waldoboro. Choose from more than 40 vacation rentals for guests traveling with pets.
How much does it cost to stay in house rentals in Waldoboro?
Experience the best of Waldoboro with our house rentals, starting at about $90 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do cabin rentals in Waldoboro have a bbq area?
Absolutely! We offer over 10 cabin rentals with a bbq area in Waldoboro. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Waldoboro?
Waldoboro has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
Do house rentals in Waldoboro have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Waldoboro. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Waldoboro have wireless internet?
Absolutely! We offer over 20 house rentals with wireless internet in Waldoboro. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for House Rentals in Waldoboro?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with a bbq area, over 10 homes with air conditioning, over 20 homes with wireless internet, and more. Indulge in the ultimate retreat, tailored to your preferences.

Waldoboro vacation rentals

Top-rated vacation rentals in Waldoboro

Vacation rentals for every style

Houses

Hotels

Unique stays

Popular amenities for Waldoboro vacation rentals

Stay near Waldoboro's top sights

Other great vacation rentals in Waldoboro

Guesthouse in South Bristol

Apartment in Boothbay

Cottage in Saint George

Place to stay in Owls Head

Cottage in Owls Head

Guesthouse in Orland

Home in Lisbon

Apartment in Edgecomb

Other great vacation rentals in Waldoboro

Guest suite in Round Pond

Home in Waldoboro

Apartment in Waldoboro

Home in Waldoboro

Cabin in Waldoboro

Farm stay in Waldoboro

Vacation home in Waldoboro

Guesthouse in Damariscotta

Quick stats about vacation rentals in Waldoboro

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Waldoboro?

Are there pet-friendly vacation rentals in Waldoboro?

How much does it cost to stay in house rentals in Waldoboro?

Do cabin rentals in Waldoboro have a bbq area?

Are there family-friendly house rentals in Waldoboro?

Do house rentals in Waldoboro have air conditioning?

Do house rentals in Waldoboro have wireless internet?

What are the most popular amenities for House Rentals in Waldoboro?

Destinations to explore