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 15 – 22

R1,784 ZAR 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.

Jul 16 – 23

R2,351 ZAR 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 11 – 18

R2,036 ZAR 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

R2,737 ZAR 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 15 – 22

R2,108 ZAR 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 12 – 19

R2,090 ZAR 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 1 – 8

R2,903 ZAR 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 14 – 21

R1,890 ZAR 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.

Dec 11 – 18

R2,258 ZAR 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.

Mar 15 – 22

R2,904 ZAR per night

Guest favorite

Apartment in Boothbay

4.96 out of 5 average rating, 259 reviews

Sunnymeade

Centrally located close to Boothbay Harbor, East Boothbay and Southport Island. Coastal Maine Botanical Gardens, Boothbay Region Land Trust's 26 hiking trails, Boothbay Railroad Village with live steam train rides and much, much more are great spots to visit.

Sep 23 – 30

R1,961 ZAR 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

R3,048 ZAR 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

Cottage in Rockport

4.95 out of 5 average rating, 165 reviews

Designer’s Coastal Retreat with Simple Luxuries

Dec 3 – 10

R2,789 ZAR per night

Guest favorite

Guesthouse in Orland

4.99 out of 5 average rating, 103 reviews

Cozy cottage in Orland Village-Penobscot Bay area

Dec 7 – 14

R1,982 ZAR 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!

Apr 15 – 22

R2,768 ZAR per night

Guest favorite

Home in Edgecomb

4.95 out of 5 average rating, 404 reviews

Sheepscot Harbour Cottage/waterview

Apr 8 – 15

R2,795 ZAR 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

Feb 11 – 18

R1,273 ZAR per night

Guest favorite

Cottage in Owls Head

4.99 out of 5 average rating, 139 reviews

Coastal Maine contemporary cottage

Oct 6 – 13

R2,750 ZAR per night

Guest favorite

Cabin in Camden

4.83 out of 5 average rating, 708 reviews

Cozy Village Cottage

Nov 17 – 24

R2,416 ZAR 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

Oct 2 – 9

R1,958 ZAR per night

Show all

Other great vacation rentals in Waldoboro

Guest favorite

Guesthouse in Georgetown

4.9 out of 5 average rating, 136 reviews

Island Alchemy Cottage

Aug 4 – 11

R2,396 ZAR per night

Superhost

Guest suite in Union

4.83 out of 5 average rating, 134 reviews

Farmhouse Suite w/ Private Entrance—Midcoast

Jan 21 – 28

R1,505 ZAR per night

Guest favorite

Home in Waldoboro

4.98 out of 5 average rating, 64 reviews

1830s Cape hosted by George & Paul

Nov 13 – 20

R1,893 ZAR per night

Guest favorite

Apartment in Waldoboro

4.97 out of 5 average rating, 86 reviews

Studio Apartment with Kitchen

Sep 7 – 14

R1,928 ZAR 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

R2,719 ZAR per night

Guest favorite

Guesthouse in Damariscotta

4.95 out of 5 average rating, 56 reviews

Private tree-top loft 5 minutes from Damariscotta.

Oct 21 – 28

R1,886 ZAR per night

Guest favorite

Cabin in Waldoboro

4.95 out of 5 average rating, 19 reviews

Country View Cottage

Jun 5 – 12

R2,990 ZAR per night

Guest favorite

Farm stay in Waldoboro

4.92 out of 5 average rating, 12 reviews

Island View Farm

May 28 – Jun 4

R1,487 ZAR per night

Show all

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
R962 ZAR 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

Cottage in Rockport

Guesthouse in Orland

Place to stay in Owls Head

Home in Edgecomb

Home in Lisbon

Cottage in Owls Head

Cabin in Camden

Apartment in Edgecomb

Other great vacation rentals in Waldoboro

Guesthouse in Georgetown

Guest suite in Union

Home in Waldoboro

Apartment in Waldoboro

Home in Waldoboro

Guesthouse in Damariscotta

Cabin in Waldoboro

Farm stay in Waldoboro

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