Search Waldoboro Cottage Rentals

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
3 Oct - 5 Oct
In two weeks
10 Oct - 12 Oct
In one month
24 Oct - 26 Oct
In two months
21 Nov - 23 Nov

Featured Cottages in Waldoboro

Pine Grove Cottages
Exterior

Pine Grove Cottages

2.5 star property
9.8 out of 10, Exceptional, (89)
"Wonderful quiet place, The Host was a great person."
The price is S$338
includes taxes & fees
29 Sept - 30 Sept
Pine Grove Cottages
Pauls Cottage in Tenants Harbor, 1 Min to Shore
Interior

Pauls Cottage in Tenants Harbor, 1 Min to Shore

3.0 star property
Pauls Cottage in Tenants Harbor, 1 Min to Shore
Historic Waldoboro House Near Lakes, Boating, Etc!
Interior

Historic Waldoboro House Near Lakes, Boating, Etc!

3.0 star property
10.0 out of 10, Exceptional, (2)
"This home is such a gem! A historic home that is updated with many modern conveniences. We’ve been to MANY AirB&B’s and this home was probably the best equipped we’ve been in! Convenient to Boothbay and lots of downeast inlets and harbors. Very quiet, but close to groceries, food and farm stands. Our only regret was not staying longer- we would have loved to grill and use the fire pit!"
Historic Waldoboro House Near Lakes, Boating, Etc!
Private Dock & Deck: Tranquil Dam Pond Cottage!
Interior

Private Dock & Deck: Tranquil Dam Pond Cottage!

3.0 star property
Private Dock & Deck: Tranquil Dam Pond Cottage!
Deck w/ Water Views: Quiet East Boothbay Retreat!
Interior

Deck w/ Water Views: Quiet East Boothbay Retreat!

3.0 star property
Deck w/ Water Views: Quiet East Boothbay Retreat!
3 Mi to Boothbay Harbor: Coastal Colorful Home!
Interior

3 Mi to Boothbay Harbor: Coastal Colorful Home!

3.0 star property
3 Mi to Boothbay Harbor: Coastal Colorful Home!
Charming Owls Head Retreat: 2 Mi to Rockland Coast
Interior

Charming Owls Head Retreat: 2 Mi to Rockland Coast

3.0 star property
Charming Owls Head Retreat: 2 Mi to Rockland Coast
Walk to Barrett's Park: Wooded Cabin w/ Grill!
Interior

Walk to Barrett's Park: Wooded Cabin w/ Grill!

3.0 star property
Walk to Barrett's Park: Wooded Cabin w/ Grill!
'sprucewold' Boothbay Harbor Cottage w/ Deck
Interior

'sprucewold' Boothbay Harbor Cottage w/ Deck

3.0 star property
'sprucewold' Boothbay Harbor Cottage w/ Deck
Idyllic Washington Retreat w/ Fire Pit & Yard
Interior

Idyllic Washington Retreat w/ Fire Pit & Yard

3.0 star property
10.0 out of 10, Exceptional, (1)
"It was great. Nice property, internet connection was poor"
Idyllic Washington Retreat w/ Fire Pit & Yard
Updated Tiny House: Walk to Wiscasset Village
Exterior

Updated Tiny House: Walk to Wiscasset Village

3.0 star property
Updated Tiny House: Walk to Wiscasset Village
Charming East Boothbay Cottage w/ Large Yard!
Interior

Charming East Boothbay Cottage w/ Large Yard!

3.0 star property
10.0 out of 10, Exceptional, (1)
"Really nice place to stay to visit Boothbay Region"
Charming East Boothbay Cottage w/ Large Yard!
On-site Pond: Spacious Family Home in Jefferson!
Interior

On-site Pond: Spacious Family Home in Jefferson!

3.0 star property
On-site Pond: Spacious Family Home in Jefferson!
Rustic Retreat Across From Lake; Family Friendly!
Interior

Rustic Retreat Across From Lake; Family Friendly!

3.0 star property
9.0 out of 10, Wonderful, (2)
"I liked that it was by the lake quiet and secluded. "
The price is S$423
includes taxes & fees
29 Sept - 30 Sept
Rustic Retreat Across From Lake; Family Friendly!
Boothbay Harbor Cabin w/ Spacious Deck & Yard!
Interior

Boothbay Harbor Cabin w/ Spacious Deck & Yard!

3.0 star property
The price is S$650
includes taxes & fees
5 Oct - 6 Oct
Boothbay Harbor Cabin w/ Spacious Deck & Yard!
Historic Friendship Boat House Near Back River!
Interior

Historic Friendship Boat House Near Back River!

3.0 star property
Historic Friendship Boat House Near Back River!
Cozy Waterfront Cottage on Montsweag Bay!
Interior

Cozy Waterfront Cottage on Montsweag Bay!

3.0 star property
Cozy Waterfront Cottage on Montsweag Bay!
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor
Outdoor dining

Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor

3.0 star property
Oceanfront Cottage w/ Deck 2 Mi to Boothbay Harbor
Riverfront Coastal Escape With Deep Water Dock!
Interior

Riverfront Coastal Escape With Deep Water Dock!

3.0 star property
Riverfront Coastal Escape With Deep Water Dock!
Peaceful Lakefront Maine Cabin w/ Sunset Views
Interior

Peaceful Lakefront Maine Cabin w/ Sunset Views

3.0 star property
Peaceful Lakefront Maine Cabin w/ Sunset Views
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Waldoboro Hotel Reviews

Ledges by the Bay

Ledges by the Bay

10/10 Excellent
"Beautiful spot with a great, clean, inviting room. "
Christina 1-night trip
Posted 2 days ago
Ledges by the Bay

Find out more about Waldoboro

Find out more about Waldoboro

Waldoboro Cottages information

Number of reviews
91
Accommodation
40 Cottages
Lowest Price
S$338
Highest Price
S$650

Frequently asked questions

How much do cottages in Waldoboro cost?
You'll pay between S$338 and S$650 per night for cottages in Waldoboro. Whatever your budget, an awesome stay is just clicks away on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in Waldoboro?
You can choose from 40 cottages in Waldoboro. No matter if you're taking a trip with the kids or planning a retreat with your best buds, Expedia will help you find the right space to enjoy the surrounding nature.
Why book your cottage in Waldoboro with Expedia?
Booking a cottage in Waldoboro is as easy as working out your travel dates and choosing an ideal place for a getaway in the outdoors. From upscale retreats to affordable stays and cottages that offer conveniences like a kitchen, Expedia has something for all tastes. As for the best deals around? We've got your back!

Explore a world of travel with Expedia

Explore a world of travel with Expedia