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Winthrop vacation rentals

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Top-rated vacation rentals in Winthrop

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

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Townhouse in Sabattus

4.84 out of 5 average rating, 147 reviews

Modern Victorian

This is a beautifully renovated, private, 2 bedroom, first floor of a duplex. The yard is fenced in and has a large deck. The unit is very light and bright and tastefully decorated. The rooms are very large and the kitchen is open to the living room. It is in a quaint little village with a little country store just steps away where you can find almish anything you need! 10 minutes from Bates College and many lakes. Hop on the highway and be in Portland in 40 minutes or the ocean in 45 minutes!

Dec 11 – 18

Guest suite in Monmouth

4.97 out of 5 average rating, 101 reviews

Welcome to The Nest - 1 bed, deck w/bath & parking

Enjoy easy access to entertainment, restaurants & shopping. Historic Cumstom Theater, local Bakery, Bar & pizzeria. Willows Awake and The Vista wedding venues w/tasting rooms. Microbrewery’s Grateful Grains & Van der Brew tap rooms w/food trucks & entertainment. Maine turnpike access for shopping;Freeport LLBean, Portland, Bath, Augusta, Hallowell & Lew/Auburn areas. Tour Bates,Bowdoin, Colby, Thomas & Husson. Golfing, boating, antiques, State Parks, hiking/walking trails,beaches & Festivals.

Nov 17 – 24

Apartment in Richmond

4.88 out of 5 average rating, 159 reviews

Designers Dream 1br Apt where class meets relax!!!

This Designers Dream 1br apartment is located in the quintessential small Maine town of Richmond. Open the door feast your eyes on this truly unique and beautiful spot and get ready to relax or explore! Richmond is home of Swan Island a great spot to explore via kayak or canoe or just grab the ferry! We're 45 min to all downtown Portland has to offer. We are an hour to Booth Bay Harbor and the beautiful botanical gardens. Popham beach is 45 min away, one of the most amazing beaches in state.

Nov 24 – Dec 1

Loft in West Gardiner

4.98 out of 5 average rating, 110 reviews

Cozy, Efficiency Apartment with Hot Tub

Keep it simple at this peaceful, centrally-located efficiency apartment. 15 minutes to Gardiner and Augusta, 15 minutes to I95/295. Less than one hour from Portland. Walk along the stream, listen to the loons or enjoy relaxing in the hot tub. If you want to paddle in a kayak, you can do that too! Eagles regularly soar overhead. Queen size bed, love seat and room enough for a pack and pay or twin air mattress. A/C, full kitchen, Keurig, microwave, toaster, dishes. Wifi and cable. Roomy parking.

May 5 – 12

Home in Litchfield

4.92 out of 5 average rating, 112 reviews

Beautiful lake house on Tacoma Lakes near Coast

Beautiful 4BR on Tacoma Lakes 50' from water, amazing views Screened in Porch w/peaceful views 3 spring fed lakes joined by 2 bridges Private dock Bring your boat or local company can rent/deliver motor boat Canoe/2 Kayaks Wifi/3 SmartTV/Alarm System FirePit, Gas Grille, Lawn Chairs Shuffleboard table Washer/Dryer Provided: linens/towels/soap/shampoo/detergent NO SMOKING-NO PETS-NO SHOES INSIDE (please) *Must sign separate water front liability waiver after booking No cameras inside or out

May 3 – 10

Home in Buckfield

4.91 out of 5 average rating, 152 reviews

The Nifty Village House

The Nifty Village House is an animal-free private home rental in the heart of Buckfield, Maine, a small New England town that sits on the Nezinscot River. This listing has been refurbished with a brand new kitchen, bathroom and laundry room. Conveniently located near Tilton's Market, Post Office, High School and more. We welcome guests with completed profiles, I.D. Verification, photo, and good reviews on Airbnb. The Nifty Village House is managed by Michael & Andrea at Niftybug Rentals.

Nov 6 – 13

Island in Monmouth

4.98 out of 5 average rating, 193 reviews

Island Glamping in a Luxury Tent in Maine

The Hemlock Haven tent overlooks Annabessacook Lake. Sleep comfortably, cook your favorite meals, nap in the hammock, bask in the glow of the fire or woodstove, listen to the calls of the loons, play on the rope swing, canoe or kayak the lake, and walk the trails of this 14 acre wooded island. We greet you at our dock on shore, ferry you and your gear to the island, and ease you into island-life until you are settled. Enjoy super clean, Superhost, Maine Guide hospitality.

Nov 7 – 14

Cabin in Litchfield

4.82 out of 5 average rating, 147 reviews

Cobbossee log cabin / post & beam

Come and enjoy this unique log cabin / post&beam just minutes walk from cobbossee stream. A wonderful place which can be enjoyed during any season, in the winter enjoy ice fishing on pleasant pond 10 minutes away, Cobbossoconte lake 20 min. or take an hours drive to the slopes to do some skiing. During the summer come enjoy the lakes and the slower pace of life, bike or run the country roads. There is a wood burning fireplace and stove, but firewood is not provided.

Dec 25 – Jan 1

Apartment in Hallowell

4.98 out of 5 average rating, 300 reviews

Two Bedroom Mid Century Modern Downtown Apartment

Experience this amazing two bedroom Mid-Century Modern apartment in Downtown Hallowell. This is newly renovated & steps away from a variety of restaurants & pubs. It has all the fun and funky charm of the early 1960’s with bright colors, rich woods, clean lines & shag rugs. All the modern comforts including stainless steel appliances, vessel sinks, soaker tub & new beds. A couple miles from the State Capital and centrally located between Brunswick and Waterville.

Nov 14 – 21

Cabin in Litchfield

4.87 out of 5 average rating, 138 reviews

Blue Loon Camp on Pleasant Pond

This is a lovely cozy camp on Pleasant Pond. Public boat access makes it a popular lake for boating and bass fishing. The camp has dock and swim float for water fun and cool breezes from the lake make it a lovely place to be in the summer. Winter time the lake accommodates ice fishing and snowmobilers. The cabin sleeps four in bedrooms and two in the loft. Get away from it all with NO wifi or television to distract from the recreational activities.

May 2 – 9

Home in Lewiston

4.99 out of 5 average rating, 138 reviews

Clean and comfortable home

First floor of newly renovated, well-stocked, single-family home in quiet, safe neighborhood. Full kitchen, 2 bedrooms each with comfortable queen-sized bed, full bathroom, on-site laundry. Shoppable art on-site :) Located less than 1 mi from Bates College and St. Mary’s Hospital. Less than 2 mi from Central Maine Medical Center. Proof of Covid-19 vaccination may be requested for all eligible to receive vaccine (including children).

Sep 17 – 24

Guesthouse in Richmond

4.9 out of 5 average rating, 137 reviews

The Studio

Welcome to our 2.5 acre haven! This studio is full of life with color that will bring your spirits up. It is a little over 400 sq. ft. with your own private entrance from the garage and above apartment, on the first floor, your own parking and not too far from the city. Richmond is a small town that sits near the Kennebec River and Swan Island where you can enjoy outdoor adventures. * Space not equipped for children *

Mar 12 – 19

Vacation rentals for every style

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Popular amenities for Winthrop vacation rentals

Laptop-friendly workspace

Air conditioning

Stay near Winthrop's top sights

FAST EDDIES DRIVE IN8 locals recommend

Hannaford Supermarket37 locals recommend

The Barn at Silver Oaks Estate3 locals recommend

Winthrop House of Pizza6 locals recommend

TJ's Pizzeria5 locals recommend

Peppers Garden & Grill6 locals recommend

Other great vacation rentals in Winthrop

Guest suite in Lewiston

4.97 out of 5 average rating, 191 reviews

Sanctuary in the City

Dec 1 – 8

Apartment in Wilton

4.86 out of 5 average rating, 105 reviews

1 Bedroom Apartment in Downtown Wilton, Maine.

May 22 – 29

Tiny home in Winthrop

5.0 out of 5 average rating, 18 reviews

Lakefront guest cottage,

Jun 16 – 23

Cabin in Winthrop

4.97 out of 5 average rating, 36 reviews

Quaint & cozy cabin in beautiful wooded setting

Jul 30 – Aug 6

Cottage in Winthrop

4.98 out of 5 average rating, 49 reviews

Family friendly, 2-Bedroom cottage with lakeview

Nov 4 – 11

Guest suite in Hallowell

5.0 out of 5 average rating, 52 reviews

Welcome to the Brown House! Hallowell studio

Sep 3 – 10

Apartment in West Gardiner

4.93 out of 5 average rating, 28 reviews

Cobbossee Lake 3 Bedroom 2 Bath Rental

Jan 4 – 11

Apartment in Augusta

4.94 out of 5 average rating, 31 reviews

Convenient, Private Apartment Near the Capitol

Apr 20 – 27

Other great vacation rentals in Winthrop

Home in Augusta

5.0 out of 5 average rating, 11 reviews

Super cute waterfront cottage

Oct 6 – 13

Cabin in Monmouth

4.84 out of 5 average rating, 19 reviews

The Woodland Lodge

Sep 19 – 26

Home in Winthrop

4.97 out of 5 average rating, 37 reviews

Breathtaking Timber-frame Lakehouse

Jan 8 – 15

Guest suite in Chesterville

4.93 out of 5 average rating, 97 reviews

Rustic Ridge

Aug 17 – 24

Home in Leeds

4.84 out of 5 average rating, 43 reviews

WillowsAwake Winery Stay

Nov 10 – 17

Home in Jay

4.96 out of 5 average rating, 53 reviews

Porky's Parsonage! 3 BR 1.5 bath Farm house. Cozy!

Dec 27 – Jan 3

Apartment in Fayette

5.0 out of 5 average rating, 12 reviews

Limberlost East

Nov 23 – 30

Home in Winthrop

4.89 out of 5 average rating, 56 reviews

Bev's Lake house.

Dec 17 – 24

Quick stats about vacation rentals in Winthrop

Total rentals
50 properties
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Pet-friendly rentals
20 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
1.4K reviews
Nightly prices starting at
$50 before taxes and fees

Frequently Asked Questions

Are there pet-friendly vacation rentals in Winthrop?
Four-legged friends are welcome in Winthrop. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Winthrop?
Yes! Work meets play with ease at over 20 vacation rentals in Winthrop featuring dedicated workspaces. Stay connected and productive in your home away from home.
Do house rentals in Winthrop have air conditioning?
Absolutely! We offer over 10 house rentals with air conditioning in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Do cabin rentals in Winthrop have wireless internet?
Absolutely! We offer over 10 cabin rentals with wireless internet in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Do house rentals in Winthrop have a bbq area?
Absolutely! We offer over 20 house rentals with a bbq area in Winthrop. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Winthrop?
Winthrop has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
How much does it cost to stay in house rentals in Winthrop?
Experience the best of Winthrop with our house rentals, starting at about $60 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
What are the most popular amenities for House Rentals in Winthrop?
Enhance your stay in our House Rentals with the most popular amenities: over 20 homes with wireless internet, over 20 homes with a bbq area, over 10 homes with air conditioning, and more. Indulge in the ultimate retreat, tailored to your preferences.

Destinations to explore