Holiday rentals in Westbrook

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Top-rated holiday rentals in Westbrook

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Guest favourite

Flat in Gorham

4.96 out of 5 average rating, 194 reviews

Cozy Private 1 Bedroom Apartment - Gorham Village

Enjoy the historical charm of one of Gorham's oldest homes. Come stay in a lovely private second floor, one bedroom apartment with private entry. Just walking distance from restaurants, the grocery store, laundromat, college campus and local trails. It offers private off-street parking for one car and it is located in the heart of Gorham village, a safe and family oriented community. Private bedroom with queen size bed and a full size futon provided. No backyard access. Full Kitchen. Full bath.

3–10 Jun

$203 SGD per night

Guest favourite

Tiny home in Portland

4.97 out of 5 average rating, 397 reviews

The Garden Cabin Tiny Home

Love gardens, pine trees, campfires, and birds? Curious about tiny homes? Our 128 sqft cozy cabin is for you! On the spectrum between camping and a hotel room, it's a chill place to call home while visiting Portland. Enjoy our garden while sipping the beverage of your choice from your private deck. It will be a unique and amazing experience and one you will remember! Bonus: 2 super friendly dogs and a cat that will be around the property during your stay. No smoking. No pets. STHR-000718-2018

30 May – 6 Jun

$206 SGD per night

Guest favourite

Guest suite in Westbrook

4.93 out of 5 average rating, 208 reviews

Awesome open space in Westbrook near Portland, ME!

Welcome!! We're excited to share our house with you! You'll get the whole ground level of the house - two very large clean modern rooms with a private entrance, bathroom, and direct yard access to the hammock, fire pit, and wildlife. Off-street parking for 2 cars, kitchenette, 300Mbit wifi, smart TV, heat, ping pong, darts, and much more! 15 mins downtown Portland ($15 Uber) 1 mile from I-95 11 mins from the airport We will give you awesome tips on everything in the area and beyond!

28 Jan – 4 Feb

$158 SGD per night

Guest favourite

Guest suite in Portland

4.95 out of 5 average rating, 113 reviews

Sunflower Retreat in North Back Cove

The Sunflower Retreat is a private, self-contained, peaceful hideaway. Located in the back half of an adorable 1920's home, this BnB space has everything you could need. A driveway leads you around to the back of the house, where a stone walkway guides you to your own private patio and entrance. A comfortable queen bed, kitchenette, full bathroom, closet, dining nook, black-out curtains, eatery, and television are included. Free street parking. Located in close proximity of many things!

11–18 Oct

$124 SGD per night

Guest favourite

Flat in South Portland

4.95 out of 5 average rating, 167 reviews

Comfortable apartment near Willard Beach!

This luxurious first floor apartment is filled with sunshine all day long and on chilly nights the gas fireplace provides a warm ambiance. We think you’ll especially enjoy sinking into the velvet covered king size bed at night and stepping into the spacious shower that includes a rainfall shower head along with a handheld ... use either or both, as you please! The kitchen is equipped with quartz countertops, solid cherry cabinets and high end stainless steel appliances.

5–12 May

$164 SGD per night

Guest favourite

Guest suite in Scarborough

4.98 out of 5 average rating, 138 reviews

Beautiful, private apartment!! Great location!

Beautiful 750 square foot in-law apartment with private entrance. Full bedroom, bathroom, kitchen (including dishwasher), washer/dryer, and garage parking. Free wi-fi, cable, and Netflix included! All essentials included in addition to beach towels, chairs, table & cooler for the beach. Private patio includes a grill for use as well (weather permitting). Great location - 10 minutes to downtown Portland, 15 minutes to multiple beaches, 5 minutes to mall & restaurants.

9–16 Dec

$165 SGD per night

Superhost

Flat in Portland

4.78 out of 5 average rating, 304 reviews

Studio w/ Patio, Sauna & Onsite Massage

Cozy daylight basement studio in the center of Rosemont. Relax with your own private patio, sauna, on-site massage & facial. Just minutes to Portland's extensive trail system. Delicious restaurants and markets within a short walk and just 2.5 miles from the historical Old Port and artsy downtown! Perfect for business and leisure! Conveniently located just 10 minutes from the Portland Jetport and less than five minutes from I-295 and I-95. STHR-000170-2018

15–22 Mar

$148 SGD per night

Guest favourite

Flat in Portland

4.93 out of 5 average rating, 556 reviews

Adorable getaway on the Eastern Promenade

Lovely third-floor apartment on the East End just steps from the glorious Eastern Promenade. Cozy and cute, this adorable spot resides in the neighborhood which boasts the best restaurants, breweries, and coffee shops in the city all within walking distance. On a quiet residential street, there is plenty of on-street parking. This apartment is on the 3rd floor of the house . **Please note that the last 9 steps leading up to the apartment are quite steep.

8–15 Dec

$131 SGD per night

Guest favourite

Guest suite in South Portland

5.0 out of 5 average rating, 170 reviews

Bright Guest Studio Near Lighthouses and Beach

This bright guest studio is steps from the Greenbelt Walkway. Walk (within 10 mins) to two lighthouses, Willard beach, Bug Light Park, Scratch Bakery, Willard Scoops ice cream and a variety of restaurants. Portland is an 8 minute drive or 20 minute bike over the bridge. The space is minimal, bright and airy with windows surrounding, an elevated bed with comfy queen mattress, fully equipped kitchen, washer/dryer and cozy couch for lounging.

29 Oct – 5 Nov

$198 SGD per night

Guest favourite

Guest house in Windham

5.0 out of 5 average rating, 218 reviews

Cottage on Black Brook Preserve

This charming cottage is thoughtfully furnished, it's your home away from home! Clean and cozy, one bedroom with queen size bed and full kitchen. Sit in front of the gas fireplace or on your own private deck overlooking the 105 acres of Black Brook Preserve. Take a hike, snowshoe or cross-country ski right outside your door. We now have new sofa, bed, refrigerator, stove, as well as shower and bathroom flooring.

29 May – 5 Jun

$172 SGD per night

Guest favourite

Guest suite in Windham

4.92 out of 5 average rating, 151 reviews

Millers Private Studio on Highland Lake

If you're looking for a quiet, cozy getaway with private Highland Lake access this is the place for you. Private deck to enjoy your morning coffee, close to everything but in a country setting. 15 minutes from 95, Portland ME and Sebago Lake Region. Small boat launch available, Swimming & Fishing . Large back yard and a great window view of the lake. Wifi 100(mbps) for a work from home atmosphere.

13–20 Jun

$157 SGD per night

Guest favourite

Guest suite in Freeport

4.95 out of 5 average rating, 198 reviews

Weather's Edge, Freeport

Come enjoy the historic charm of South Freeport. This antique home and cozy accommodation await you, featuring a private entrance, private room, private full bath, t.v. with cable, and wi-fi. This is a second-floor room, accessed from a dramatic original (steep) staircase, and is conveniently located in an area of lovely homes, with Freeport Village just five minutes away.

18–25 May

$105 SGD per night