Holiday rentals in Waldoboro

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Top-rated holiday rentals in Waldoboro

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Guest suite in Thomaston

4.86 out of 5 average rating, 109 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.

12–19 Dec

$125 SGD per night
Guest favourite

Flat in Edgecomb

4.91 out of 5 average rating, 296 reviews

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

Bright, cozy apartment, surrounded by deep woods, completely separate from our home, w/ its own entrance, yet we are available if you need us. Located between Boothbay, Damariscotta, & Wiscasset, 1 mile from Route 1 and 27, on 13 acres, abutting 100s of acres of preserve land - provides the best of both worlds - peaceful woods, but less than 15 minutes from restaurants, shops & activities, plus, dedicated WiFi /2 Smart TVs. While dogs are welcome we can’t host feline guests due to allergies.

21–28 Oct

$134 SGD per night
Guest favourite

Flat 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.

5–12 May

$125 SGD per night

Popular amenities for Waldoboro holiday rentals

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 Brewery23 locals recommend

Other great holiday rentals in Waldoboro

Guest favourite

Cabin in Edgecomb

4.87 out of 5 average rating, 855 reviews

The Highland Cottage on Sheepscot

18–25 Mar

$211 SGD per night
Guest favourite

Cabin in Freedom

4.9 out of 5 average rating, 288 reviews

Cozy Lakefront Cabin in Freedom, ME

4–11 Dec

$111 SGD per night
Guest favourite

Cabin in Camden

4.83 out of 5 average rating, 702 reviews

Cozy Village Cottage

23–30 Dec

$169 SGD per night
Guest favourite

Flat in Searsmont

4.97 out of 5 average rating, 108 reviews

Searsmont Studio

13–20 Apr

$105 SGD per night
Guest favourite

Cottage in Edgecomb

4.9 out of 5 average rating, 104 reviews

Spectacular Water View Cottage

7–14 Nov

$184 SGD per night
Superhost

Guest suite in Union

4.83 out of 5 average rating, 134 reviews

Farmhouse Suite w/ Private Entrance—Midcoast

25 Nov – 2 Dec

$114 SGD per night
Guest favourite

Guest house in Orland

4.99 out of 5 average rating, 102 reviews

Cozy cottage in Orland Village-Penobscot Bay area

12–19 Feb

$132 SGD per night
Guest favourite

Home in Waldoboro

4.98 out of 5 average rating, 61 reviews

1830s Cape hosted by George & Paul

8–15 Dec

$133 SGD per night
Guest favourite

Flat in Waldoboro

4.97 out of 5 average rating, 86 reviews

Studio Apartment with Kitchen

22–29 Aug

$140 SGD per night
Guest favourite

Home in Waldoboro

5.0 out of 5 average rating, 47 reviews

Small But Mighty (Elegant) Rural Retreat

23–30 Jun

$192 SGD per night
Guest favourite

Cabin in Waldoboro

4.95 out of 5 average rating, 19 reviews

Country View Cottage

13–20 Dec

$210 SGD per night
Guest favourite

Cabin in Union

5.0 out of 5 average rating, 23 reviews

The Modern Beaver Cottage -Escape from it All

4–11 Nov

$158 SGD per night

Quick stats about holiday rentals in Waldoboro

Total rentals

70 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

$67 SGD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Lincoln County
  5. Waldoboro