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Top Tours in Winthrop

Portland Small-Group City and History Tour
Portland Small-Group City and History Tour
10
Excellent
1505 Reviews
5-Star Rating Recommendation
From
US $69Per Person
Reserve
The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local
The Real Portland Tour: City and 3 Lighthouses Historical Tour with a Real Local
10
Excellent
1505 Reviews
5-Star Rating Recommendation
From
US $69Per Person
Reserve
Portland City Trolley and Lighthouse Tour
Portland City Trolley and Lighthouse Tour
10
Excellent
1031 Reviews
5-Star Rating Recommendation
From
US $54Per Person
Reserve
Maine: Downtown Portland City and Lighthouse Tour
Maine: Downtown Portland City and Lighthouse Tour
10
Excellent
956 Reviews
5-Star Rating Recommendation
From
US $91Per Person
Reserve
Portland, Maine Guided 1-Hour Tour on a Vintage Fire Engine
Portland, Maine Guided 1-Hour Tour on a Vintage Fire Engine
10
Excellent
864 Reviews
5-Star Rating Recommendation
From
US $45Per Person
Reserve
Portland Harbor Sightseeing Cruise
Portland Harbor Sightseeing Cruise
10
Excellent
711 Reviews
5-Star Rating Recommendation
From
US $54Per Person
Reserve
Portland Hidden Histories Small-Group Walking Tour
Portland Hidden Histories Small-Group Walking Tour
10
Excellent
523 Reviews
5-Star Rating Recommendation
From
US $54Per Person
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Portland History Walking Tour
Portland History Walking Tour
10
Excellent
502 Reviews
5-Star Rating Recommendation
From
US $48Per Person
Reserve
Old Port Culinary Walking Tour from Portland
Old Port Culinary Walking Tour from Portland
10
Excellent
425 Reviews
5-Star Rating Recommendation
From
US $159Per Person
Reserve
Camden: Windjammer Sunset Sailing Tour
Camden: Windjammer Sunset Sailing Tour
10
Excellent
425 Reviews
5-Star Rating Recommendation
From
US $64Per Person
Reserve
Windjammer Classic Day Sail from Camden, Maine
Windjammer Classic Day Sail from Camden, Maine
10
Excellent
407 Reviews
5-Star Rating Recommendation
From
US $59Per Person
Reserve
Portland Sightseeing Lighthouse Cruise
Portland Sightseeing Lighthouse Cruise
10
Excellent
258 Reviews
5-Star Rating Recommendation
From
US $39Per Person
Reserve
Find A Tour In Winthrop

All Tours in Winthrop

Whether you love exploring landmarks or tasting local cuisine, you’ll find endless adventures here.

Most popular tours in Winthrop

See all 229+ Tours in Winthrop
Portland Tall Ship Cruise on Casco Bay

Portland Tall Ship Cruise on Casco Bay

9
Excellent
236 Reviews
5-Star Rating Recommendation
From
US $101Per Person
Reserve
Portland Maine Traditional Windjammer Sailing Tour

Portland Maine Traditional Windjammer Sailing Tour

9
Excellent
236 Reviews
5-Star Rating Recommendation
From
US $99Per Person
Reserve
Afternoon Windjammer Cruise Along the Coast of Portland Maine

Afternoon Windjammer Cruise Along the Coast of Portland Maine

9
Excellent
186 Reviews
5-Star Rating Recommendation
From
US $69Per Person
Reserve
Old Port "Seafood Lovers" Walking Lunch Tour in Portland, Maine

Old Port "Seafood Lovers" Walking Lunch Tour in Portland, Maine

10
Excellent
148 Reviews
5-Star Rating Recommendation
From
US $160Per Person
Reserve
Portland, Maine: Black History Guided Walking Tour

Portland, Maine: Black History Guided Walking Tour

10
Excellent
145 Reviews
5-Star Rating Recommendation
From
US $54Per Person
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Portland Black History Walking Tour

Portland Black History Walking Tour

10
Excellent
145 Reviews
5-Star Rating Recommendation
From
US $54Per Person
Reserve
Sunset Windjammer Cruise Along the Coast of Portland Maine

Sunset Windjammer Cruise Along the Coast of Portland Maine

10
Excellent
144 Reviews
5-Star Rating Recommendation
From
US $77Per Person
Reserve
Sunset Lighthouse Cruise Tour from Casco Bay

Sunset Lighthouse Cruise Tour from Casco Bay

10
Excellent
134 Reviews
5-Star Rating Recommendation
From
US $56Per Person
Reserve
Casco Bay, Portland Maine: Sunset Sightseeing Cruise Tour

Casco Bay, Portland Maine: Sunset Sightseeing Cruise Tour

10
Excellent
130 Reviews
5-Star Rating Recommendation
From
US $56Per Person
Reserve
Lighthouse Bicycle Tour from South Portland with 4 Lighthouses

Lighthouse Bicycle Tour from South Portland with 4 Lighthouses

10
Excellent
114 Reviews
5-Star Rating Recommendation
From
US $115Per Person
Reserve
Portland Lighthouse Small-Group Bicycle Tour

Portland Lighthouse Small-Group Bicycle Tour

10
Excellent
114 Reviews
5-Star Rating Recommendation
From
US $115Per Person
Reserve
Sunset Sea Kayak Tour on Casco Bay

Sunset Sea Kayak Tour on Casco Bay

10
Excellent
103 Reviews
5-Star Rating Recommendation
From
US $60Per Person
Reserve
See all 229+ Tours in Winthrop

Other tours in Winthrop

Discover Portland City and Lighthouse Tour
Discover Portland City and Lighthouse Tour
10
Excellent
1031 Reviews
5-Star Rating Recommendation
From
US $57Per Person
Reserve
Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour
Portland Explorer | Maine History, Culture, & 3 Lighthouses Tour
10
Excellent
956 Reviews
5-Star Rating Recommendation
From
US $91Per Person
Reserve
Vintage Fire Truck Sightseeing Tour of Portland Maine
Vintage Fire Truck Sightseeing Tour of Portland Maine
10
Excellent
864 Reviews
5-Star Rating Recommendation
From
US $45Per Person
Reserve
Harbor Lights and Sights Cruise
Harbor Lights and Sights Cruise
10
Excellent
712 Reviews
5-Star Rating Recommendation
From
US $57Per Person
Reserve
Portland, Maine: Hidden Histories Guided Walking Tour
Portland, Maine: Hidden Histories Guided Walking Tour
10
Excellent
523 Reviews
5-Star Rating Recommendation
From
US $54Per Person
Reserve
A Walk Through Time Tour in Portland
A Walk Through Time Tour in Portland
10
Excellent
502 Reviews
5-Star Rating Recommendation
From
US $49Per Person
Reserve
Windjammer Classic Sunset Sail from Camden, Maine
Windjammer Classic Sunset Sail from Camden, Maine
10
Excellent
425 Reviews
5-Star Rating Recommendation
From
US $65Per Person
Reserve
Port City Lights Cruise
Port City Lights Cruise
10
Excellent
259 Reviews
5-Star Rating Recommendation
From
US $39Per Person
Reserve
Portland Walking Food Tour – Warm Donuts, History & Hidden Gems
Portland Walking Food Tour – Warm Donuts, History & Hidden Gems
10
Excellent
189 Reviews
5-Star Rating Recommendation
From
US $70Per Person
Reserve
Portland Downtown & Old Port Donut Tasting Walking Tour
Portland Downtown & Old Port Donut Tasting Walking Tour
10
Excellent
181 Reviews
5-Star Rating Recommendation
From
US $79Per Person
Reserve
Portland Lighthouses Small-Group Bike Tour with Lobster Roll
Portland Lighthouses Small-Group Bike Tour with Lobster Roll
10
Excellent
150 Reviews
5-Star Rating Recommendation
From
US $165Per Person
Reserve
Portland Bicycle Tour with 5 Lighthouses and XL Lobster Roll
Portland Bicycle Tour with 5 Lighthouses and XL Lobster Roll
10
Excellent
150 Reviews
5-Star Rating Recommendation
From
US $165Per Person
Reserve
Show all 229+ Tours in Winthrop

Top-rated places to stay near Winthrop

Find the perfect place to stay in Winthrop with Varoom. Choose from a wide range of vacation rentals, cottages, condos, and private villas - many offering top amenities and great value.

Winthrop
Winthrop63+ Properties
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House
Peaceful Fisherman's Paradise w/Deck + Fire Pit!
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like-icon10.0
Exceptional
(32 Reviews)
2 Bedrooms 1 Bath 100 Guests 2000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Ocean View
    Ocean View
More amenities
US $292/Night 7 Nights - US $2,042
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House
Little Landing Cottage On Cobbossee Lake
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like-icon10.0
Exceptional
(5 Reviews)
1 Bedroom 1 Bath 4 Guests 828.82 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • View
    View
More amenities
US $393/Night 7 Nights - US $2,751
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House
Little Landing Cottage-gorgeous View BBQ Wi-fi
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like-icon10.0
Exceptional
(1 Review)
1 Bedroom 1 Bath
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $754/Night 7 Nights - US $5,278
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Cabin
Escape to our cozy Winthrop cabin on Dexter Pond
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like-icon10.0
Exceptional
(25 Reviews)
2 Bedrooms 1 Bath 5 Guests
  • Ocean View
    Ocean View
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $249/Night 7 Nights - US $1,743
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House
Cozy Keyes Cottage
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like-icon10.0
Exceptional
(3 Reviews)
2 Bedrooms 1 Bath 5 Guests 904.17 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • View
    View
More amenities
US $550/Night 7 Nights - US $3,852
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House
Enjoy Sunset views on tranquil Dexter Pond
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like-icon10.0
Exceptional
(21 Reviews)
2 Bedrooms 1 Bath 4 Guests 1000 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $346/Night 7 Nights - US $2,423
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Cottage
Cozy Keyes Cottage | Lakefront Dock Kayaks
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like-icon10.0
Exceptional
(13 Reviews)
2 Bedrooms 1 Bath 5 Guests 744 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $669/Night 7 Nights - US $4,684
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Cabin
Cozy Cabin on Cobbossee Lake near Lakeside Marina
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like-icon10.0
Exceptional
(6 Reviews)
2 Bedrooms 1 Bath 6 Guests
  • Oceanfront
    Oceanfront
  • Ocean View
    Ocean View
More amenities
US $237/Night 7 Nights - US $1,658
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Apartment
NEW Construction! 2-BR Apt walking distance to The Barn at Silver Oaks, Winthrop
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like-icon10.0
Exceptional
(3 Reviews)
2 Bedrooms 1 Bath 6 Guests 1200 ft²
  • Fireplace/Heating
    Fireplace/Heating
  • Balcony/Terrace
    Balcony/Terrace
More amenities
US $411/Night 7 Nights - US $2,877
View Deal
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