Search Vacation Homes in Waldoboro

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 458 Vacation Homes in Waldoboro with updated reviews, rates, and availability.

Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views
9.4 out of 10, Exceptional, (25)
"This is a great home with lots of room, natural light, comfortable bedrooms and a back deck we'd spend hours on in the evenings. Having a full bedroom and bathroom on the first floor and the two bedrooms and bathrooms upstairs also gave everyone privacy and downtime. The area is really quiet and walking distance from a path that runs alongside the water. The home is comfortable and roomy enough that being rained in for a day is no problem, and getting out to surrounding places is easy. "
Dog-friendly beach house with WiFi, private washer/dryer, deck, beautiful views
Cozy Maine home. River view. Minutes from ocean, lighthouses and sights.
10.0 out of 10, Exceptional, (4)
"The property was close to everything and so comfortable. We had two couples but could comfortably sleep more. All three bathrooms had large showers and were roomy. Beds were very comfortable. Would stay again in a minute and recommend highly. "
Cozy Maine home. River view. Minutes from ocean, lighthouses and sights.
Beautiful Antique Waterfront Property On Round Pond Harbor - Sleeps 7
10.0 out of 10, Exceptional, (60)
"Steep and narrow steps to bedrooms. We Are older but rented it anyway and are so glad we did. The place is so peaceful, beautiful, so well appointed and decorated. We had to be forced out with threats of legal action 😁"
Beautiful Antique Waterfront Property On Round Pond Harbor - Sleeps 7
THE BARN ON PASCAL... A lovely circa 1900 refurbished barn.
10.0 out of 10, Exceptional, (40)
"This place met all of our needs. Super convenient. Super clean and amazing in every way. We will be back"
THE BARN ON PASCAL... A lovely circa 1900 refurbished barn.
Oceanfront home on 6 acres with multi-level deck & spectacular view
9.8 out of 10, Exceptional, (7)
Oceanfront home on 6 acres with multi-level deck & spectacular view
More then a Motel With Garden , Renovated Rooms at heart of Boothbay
2.0 star property
The price is $140
includes taxes & fees
$128 per night
Sep 25 - Sep 26
More then a Motel With Garden , Renovated Rooms at heart of Boothbay
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views
10.0 out of 10, Exceptional, (107)
"Such a beautiful property! Our flight got a bit late and Alex and Siobhán were gracious and kind. They met us with the keys and went over the information needed. Because it was dark when we arrived, we were so amazed to see the beautiful views when we awoke. We were close to shops and amazing restaurants. I would definitely recommend!"
Oceanfront Private Ocean Access to a small sandy beach Unobstructed Water Views
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina
9.4 out of 10, Exceptional, (46)
"We had a two-night stay. And since we were so close to the harbor, it made for easy walks to the points of interest nearby; easy walk to the harbor. We could see the harbor from out the windows. We cooked on the newer clean grill. You need to sign into your own Roku account to use the TV which we did to see the Olympics."
Newly Renovated Haven w/ Deck, Near Downtown: Walk to Shops, Dining & Marina
Make Shimmering River Retreat your Maine Coastal getaway!
9.6 out of 10, Exceptional, (30)
"We have rented many properties for our yearly family vacation but this was by far our favorite! We've already rebooked for next year. The location, the size of the property, the pool, the outdoor areas... everything was amazing! The adults loved the deepwater dock, the kayaks and canoe. The little kids loved the pool. There were many places to go visit locally but we were able to come back to the peace and tranquility of the house. The guest cottage was a big hit for the grandkids!"
Make Shimmering River Retreat your Maine Coastal getaway!
Downtown Boothbay Harbor, 2-Story Cottage
9.8 out of 10, Exceptional, (13)
"House was a short walk to Boothbay Harbor. Owners were great on communication with us prior to check in. House condition was good. It is need in need of a paint job and a few repairs. The price for a 2 night stay was great. Only issue for me was that bathroom has no door and located upstairs in bedroom. It only had a light weight curtain. So when my spouse or myself had to use it during the night turning the light on in the bathroom woke up the other person. So bring a nightlight to plug in...
The price is $304
includes taxes & fees
$279 per night
Oct 6 - Oct 7
Downtown Boothbay Harbor, 2-Story Cottage
Oceanfront Adj. Resort +Lighthouse: Enjoy Beaches, Hikes, Quaint Shops &Lobster!
9.8 out of 10, Exceptional, (18)
"Very clean and well stocked property. All communications with David were prompt. I’ve been to the Samoset several times and the views are awesome however this property is not oceanfront nor does it have an ocean view so it was somewhat of a disappointment. Still you’re very close to all the Samoset amenities and a short drive to Rockland, Rockport, and Camden. "
Oceanfront Adj. Resort +Lighthouse: Enjoy Beaches, Hikes, Quaint Shops &Lobster!
Waterfront Cottage on Tidal Cove with Dock
9.8 out of 10, Exceptional, (41)
"I wanted to stay in Maine for 3 weeks - I chose this location so I could be sometimes by myself and sometimes with friends. From this location, there is a lot to do locally as well as within 1 hour drive if desired. About 40 minutes to nearest Amtrak station in Brunswick if friends are visiting. Locally - many preserves to walk, kayak/paddleboard at house, minutes to Boothbay Harbor - schooner and wildlife boats, restaurants. This house was great for me as it was not too big when I was by...
Waterfront Cottage on Tidal Cove with Dock
Newly Renovated Charming House with Cozy Fireplace & Outdoor Entertainment Areas
2.0 star property
Newly Renovated Charming House with Cozy Fireplace & Outdoor Entertainment Areas
Cozy Cottage with Ocean Views and Dog-Friendly Charm
2.0 star property
10.0 out of 10, Exceptional, (2)
"Liked having the cottage to our selves and home like feeling. The only thing that was not there was a outdoors firepit or fireplace to enjoy more of the outdoors but we loved it and might even try to get back soon"
Cozy Cottage with Ocean Views and Dog-Friendly Charm
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
8.0 out of 10, Very Good, (14)
"Beautiful place. Loons, eagles, Ospreys, and good fishing. No A/C made a couple of days miserable when heat and humidity was in the mid-nineties. Many fans available, though. Would be more ethical to let people know before booking that tap water is not drinkable. Saying a kayak is available is a bit of a stretch (small plastic boat)."
Dog-friendly lakefront home with dock, fireplace, firepit, lake views, & 1 kayak
Slow Down & Go Back in Time-Relax Completely in Our Maine Home
9.6 out of 10, Exceptional, (63)
"An immaculate well appointed cottage that was an absolute delight. Close to everything, including Colonial Pemaquid, Pemaquid Beach and the lighthouse."
Slow Down & Go Back in Time-Relax Completely in Our Maine Home
Private Oceanfront Home on 10 Acres -- 2 Fireplaces, 4 Decks & Grill
8.8 out of 10, Excellent, (19)
"the house location and the house itself are simply magnificent. The house could stand a few improvements. The deck furniture is simply terrible. The Small table and the chairs are old and rusted. One chair was totally unusable. This is our second stay there and are planning on another stay. We are hoping for a new deck set."
Private Oceanfront Home on 10 Acres -- 2 Fireplaces, 4 Decks & Grill
Comfortable, Close to Town Home, with Oceanview.
9.6 out of 10, Exceptional, (60)
"Enjoyed our stay"
The price is $417
includes taxes & fees
$383 per night
Oct 2 - Oct 3
Comfortable, Close to Town Home, with Oceanview.
Multi-unit with oar & boat house with private dock & kayaks
9.0 out of 10, Wonderful, (21)
"Stayed for a week. You can’t beat the location! Fabulous spot with a dock and deck right on the Harbor. 5 min walk into town. The property is a great set up if you’ve got a large party. We were 10 and it was perfect. There are a few things that need some work… Only one bathroom had a bathmat and the 2nd floor shower in the main house is difficult to navigate without drenching the floor with its multitude of curtains and no shelf or hanging caddy to put soap and shampoo. The bedrooms, including...
Multi-unit with oar & boat house with private dock & kayaks
Quintessential Maine Oceanfront home
10.0 out of 10, Exceptional, (70)
"Had a wonderful time at the home. The views are just beautiful!"
Quintessential Maine Oceanfront home
Don't see what you're looking for?
See all available properties in Waldoboro
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.
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Waldoboro

Trade Winds on the Bay
3.0 star property
7.8 out of 10, Good, (100)
"I have stayed at the Tradewinds many times and it is very conveniently located with a great view of the harbor. It also now has a nice little coffee bar right in the hotel. "
The price is $150
includes taxes & fees
$138 per night
Oct 20 - Oct 21
Trade Winds on the Bay
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
8.6 out of 10, Excellent, (39)
"GORGEOUS house and view! Very spacious and accommodating. Things you should know before booking is that it is about an hour away from anything and everything. House could use some more TV's if you're going with children, pinball machines did not work and neither did "workout equipment" which was an elliptical and treadmill. One of the showers did not work and some of the fans that were provided did not either. I think its a tad over priced for its distance to do things but the views from...
Delightful oceanfront home with amazing views, wrap-around deck & two fireplaces
Unique oceanfront home with a deck, tons of natural light, & amazing views
8.6 out of 10, Excellent, (49)
"Beautiful property. Saw seals from living room catching fish. Front door did not lock but it’s a safe neighborhood but a bit isolated. Kitchen is well equipped for cooking. Laundry facilities were a great help! Gorgeous views of the water and excellent service and communication."
Unique oceanfront home with a deck, tons of natural light, & amazing 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.