Holiday rentals in Rockland

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Top-rated holiday rentals in Rockland

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

Guest favourite
Home in Rockland
Rockland Relaxing Retreat/Walk to Town (STR23-36)
Come enjoy the natural beauty of Coastal Maine as well as lobster, art, and wine in Rockland, Maine. Stroll to Rockland’s restaurants, bakeries, shops, museums, breweries, and ferry terminal from this comfortable 3-bedroom, 1.5 bath house. The house has 1 King bed, 1 Queen bed, and 1 twin/trundle bed. It is kid-friendly with a large back yard and a fully-equipped kitchen and smart TV, (but no cable and no AC), and PS3 with games. Camden is nearby and has a ski resort. 10% military discount.
17–24 Nov
$349 SGD per night
4.92 out of 5 average rating, 159 reviews
Guest favourite
Guest suite in Thomaston
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.
17–24 Sep
$108 SGD per night
4.86 out of 5 average rating, 109 reviews
Guest favourite
Home in Rockland
Downtown-Walk to All Things Rockland
Cute, convenient, and clean recently renovated 1930’s cottage has two bedrooms, sleeps 4, a private backyard, and is within walking distance to downtown, restaurants, nightlife, co-op & supermarket, museums, shops, art galleries, Harbor Park, ferry and the waterfront. Enjoy off-street parking and an ocean view with the sun glistening off the harbor at the end of the street. This is a perfect home-base for a coastal Maine vacation and festivals. Discounts offered for weekly and monthly stays!
29 Mar – 5 Apr
$244 SGD per night
4.95 out of 5 average rating, 312 reviews

Popular amenities for Rockland holiday rentals

Stay near Rockland's top sights

Harbor Park5 locals recommend
Maine Lobster Festival13 locals recommend
Walmart Supercenter10 locals recommend
Maine Lighthouse Museum22 locals recommend
Claws33 locals recommend
Archer’s on the Pier41 locals recommend

Other great holiday rentals in Rockland

Guest favourite
Cabin in Rockport,
Ragged Mountain Retreat
7–14 May
$186 SGD per night
4.94 out of 5 average rating, 109 reviews
Guest favourite
Flat in Rockport
Centrally Located Apartment! Rockport, Maine
27 Jan – 3 Feb
$154 SGD per night
4.94 out of 5 average rating, 193 reviews
Guest favourite
Cottage in Saint George
Hidden Haven A Rustic Retreat In St. George, Maine
18–25 Sep
$201 SGD per night
4.96 out of 5 average rating, 188 reviews
Guest favourite
Flat in Rockland
Harbor Duet Apartment
5–12 Jul
$181 SGD per night
4.97 out of 5 average rating, 192 reviews
Guest favourite
Tiny home in Rockland
Simplicity-Just what you need! STR23-70
13–20 May
$145 SGD per night
4.96 out of 5 average rating, 45 reviews
Guest favourite
Guest suite in Thomaston
Midcoast Retreat with Fireplace Near Downtown
27 May – 3 Jun
$122 SGD per night
4.93 out of 5 average rating, 58 reviews
Guest favourite
Flat in Rockland
SALTY CAPE: In-town, coastal + relaxing, Rockland
25 Feb – 4 Mar
$304 SGD per night
5.0 out of 5 average rating, 58 reviews
Guest favourite
Flat in Rockland
1901 Charm in Downtown Rockland
4–11 Aug
$406 SGD per night
4.93 out of 5 average rating, 40 reviews
Guest favourite
Cottage in Saint George
Quiet Cove Cottage Retreat
20–27 Sep
$212 SGD per night
4.95 out of 5 average rating, 37 reviews
Guest favourite
Home in Rockport
Seaside House/Downstairs
21–28 Feb
$435 SGD per night
4.93 out of 5 average rating, 98 reviews
Guest favourite
Guest suite in Owls Head
Private Maine Farmhouse Suite
11–18 Jun
$131 SGD per night
4.92 out of 5 average rating, 98 reviews
Guest favourite
Home in Owls Head
Extreme Oceanfront House
17–24 Jan
$569 SGD per night
4.94 out of 5 average rating, 36 reviews

Quick stats about holiday rentals in Rockland

Total rentals

150 properties

Rentals with a pool

30 properties have a pool

Pet-friendly rentals

40 properties allow pets

Family-friendly rentals

80 properties are a good fit for families

Total number of reviews

6.1K reviews

Nightly prices starting at

$54 SGD before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Maine
  4. Knox County
  5. Rockland