The 5 best Bed and Breakfast Inns in Winthrop, United States

April 20, 2023 Stefan Strunk

Discover the best Bed and Breakfast Inns in Winthrop, Maine including The Roost Bed & Breakfast, Cobbossee Motel, Annabessacook Farm Bed & Breakfast, Tallwood Cottages, Maple Tree Inn Bed and Breakfast.
Things to do in Winthrop

1. The Roost Bed & Breakfast

195 Annabessacook Rd, Winthrop, ME 04364-3832
Excellent
91%
Good
9%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5 based on 35 reviews

The Roost Bed & Breakfast

The Roost Bed & Breakfast is located in the beautiful lakes region of Winthrop, Maine. Situated on 16 acres of open fields, The Roost is the perfect place to visit for recreation or relaxation. Come enjoy our new 5x8 outdoor shower, private patio, or venture out to one of the three lakes within a 5 minute drive. Your hosts Dave and Shirley look forward making your stay unforgettable. It's worth the ride to the countryside!

Family Road trip

Reviewed By Rachel C

We were passing through this area on a family road trip. You have a beautiful house & the location was perfect for us. Our kids enjoyed your back yard & cat! Thank you for your hospitality and the breakfast was delicious!

2. Cobbossee Motel

7 Carlton Pond Rd, Winthrop, ME 04364-3106
Excellent
55%
Good
20%
Satisfactory
10%
Poor
0%
Terrible
15%
Overall Ratings

4 based on 20 reviews

Cobbossee Motel

Quiet, family-owned lodging in Winthrop, Maine. We specialize in making your extended stay comfortable with in -room amenities.

The worst place to stay in the WORLD!

Reviewed By kathyaG4700JY

If I could give this hotel a zero I would. The guy who manages the place is something else. You go to talk to him and he talks through his ring doorbell. When he comes to my door he just yells outside to open the door. The oven wasn't working in the stove and he refused to do anything about it. Then the stove itself wouldn't work. Staff have pretty much gone in my room every time I leave. I came back yesterday and the cable/internet box was gone and the telephone was gone. I'm also missing personal items. I also found out that the smoke detectors are empty - there are not working smoke detectors in the rooms. I wouldn't be surprised if they have cameras in the room spying on guests. They have lied to me, and I believe have stolen from me. If you don't want to get ripped off - LOOK ELSEWHERE. This hotel is the pits and no place to spend money on for vacation. BEWARE!!!!!

3. Annabessacook Farm Bed & Breakfast

192 Annabessacook Rd, Winthrop, ME 04364-3839
Excellent
40%
Good
20%
Satisfactory
40%
Poor
0%
Terrible
0%
Overall Ratings

4 based on 5 reviews

Enjoy a farm vacation at our restored 1810 farmhouse set on 25 acres with frontage on Lake Annabessacook. In summer, enjoy private swimming, boating, and fishing at the lake, horseback riding, hiking, or reclining in the sun by the pond. Winter brings cross-country skiing, snowmobiling, or day trips to downhill skiing. Gourmet meals with farm fresh eggs, a sauna and whirlpool during any season. 10 miles west of Augusta and 15 miles northeast of Lewiston.

Down Home!

Reviewed By diananunnaley

Annabessacook Farm & B & B offers the best setting for a very comfortable stay. Enjoy hearing the sounds and breathing in the memories of growing up on a farm- or delight to experience these rural senses for your first time. Breakfasts are delicious and not on a schedule. There is a lake within walking distance with floats available on the property. And don’t forget to pick up your veggies and eggs from the stand (or pick your own!) before the drive home.

4. Tallwood Cottages

Tallwood Drive, Winthrop, ME 04364
Excellent
100%
Good
0%
Satisfactory
0%
Poor
0%
Terrible
0%
Overall Ratings

5 based on 1 reviews

Tallwood Cottages are lakeside cottages on Maranacook Lake in central Maine. They are available to rent by the week, with a discount for multiple week stays. Retired couples and families with children often rent for 2 - 4 weeks and come back every summer to enjoy a private lake setting with a lot of shoreline (~2 miles of this privately-owned peninsula) to explore, birds to watch (eagles, osprey, loons, heron), woods to walk through, and a beautiful lake to kayak or canoe around. A small sandy beach area and dock is shared by the cottage renters and owner. The cottages were mostly built in the late 1800s/early 1900s, so are rustic but renovated in recent years.

A connection with the wilderness.

Reviewed By Anthony F

My stay at Tallwood Cottages helped me disconnect from work and connect with nature. The lake and its surroundings were beautiful to look at and swim in and the animals which include a bald eagle were wonderful sights to see.

5. Maple Tree Inn Bed and Breakfast

34 High St, Winthrop, ME 04364-1307

An all natural Bed & breakfast featuring organic fare and meals prepared specific to your dietary restrictions. Quiet, secluded, yet within walking distance of lake and fine dining. Located off Main Street. On site all natural store, soap and candle factory, primitives, smalls.

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