New Gloucester Vacation Rentals

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Sep 19 - Sep 21
In two months
Oct 31 - Nov 2
In three months
Nov 28 - Nov 30
In four months
Dec 26 - Dec 28

Browse Select New Gloucester Vacation Homes

Our top choices for New Gloucester vacation homes

The Barnhouse with hot tub
Microwave, oven, stovetop, dishwasher

The Barnhouse with hot tub

10.0 out of 10, Exceptional, (3)
"Thank you Bethany for a most wonderful stay. What a beautiful property you have here. We really loved the opportunity to enjoy the barn house. Hope you and your family have an awesome summer. "
The price is CA $260
CA $493 total
includes taxes & fees
Sep 4 - Sep 5
The Barnhouse with hot tub
Private Entrance Residential Portland
Fridge, microwave, oven, stovetop

Private Entrance Residential Portland

9.0 out of 10, Wonderful, (4)
"Check in was simple. Quaint place. "
The price is CA $144
CA $244 total
includes taxes & fees
Sep 2 - Sep 3
Private Entrance Residential Portland
Manor Suite,cozy newly renovated,downtown & beach
Property grounds

Manor Suite,cozy newly renovated,downtown & beach

The price is CA $102
CA $208 total
includes taxes & fees
Sep 2 - Sep 3
Manor Suite,cozy newly renovated,downtown & beach
Willard Beach–Private Apt Near Portland & Parks
Interior

Willard Beach–Private Apt Near Portland & Parks

10.0 out of 10, Exceptional, (2)
"Excellent in every way."
The price is CA $141
CA $344 total
includes taxes & fees
Sep 8 - Sep 9
Willard Beach–Private Apt Near Portland & Parks
Charming private 3-bedroom on 3 acres in Sebago, Pool, Hot Tub, Large Firepit
Outdoor spa tub

Charming private 3-bedroom on 3 acres in Sebago, Pool, Hot Tub, Large Firepit

10.0 out of 10, Exceptional, (2)
"The whole stay was perfect from checking in to departure. The pool was great and my 2 granddaughters enjoyed it. The house was very clean and everything stalked fully. Definitely would stay here again."
The price is CA $383
CA $629 total
includes taxes & fees
Sep 28 - Sep 29
Charming private 3-bedroom on 3 acres in Sebago, Pool, Hot Tub, Large Firepit
An Authentic Clean & Cozy Maine Homestay
3 bedrooms, desk, iron/ironing board, free WiFi

An Authentic Clean & Cozy Maine Homestay

9.8 out of 10, Exceptional, (60)
"The host provided excellent information and was very easy to communicate with. The property was very comfortable and clean. "
The price is CA $158
CA $258 total
includes taxes & fees
Sep 3 - Sep 4
An Authentic Clean & Cozy Maine Homestay
Camp Forever cottage
Outdoor dining

Camp Forever cottage

9.6 out of 10, Exceptional, (52)
"Great stay. My husband and I were there for 4 days. Peaceful and quiet. Lovely views. Just perfect for the two of us. Short drive to area sites, businesses and restaurants."
The price is CA $199
CA $385 total
includes taxes & fees
Oct 1 - Oct 2
Camp Forever cottage
Luxury on Back Cove - Three Gables
Fridge, microwave, oven, stovetop

Luxury on Back Cove - Three Gables

10.0 out of 10, Exceptional, (4)
"GoodLocation, very clean. Would stay again "
The price is CA $266
CA $625 total
includes taxes & fees
Sep 3 - Sep 4
Luxury on Back Cove - Three Gables
Sauna & fire table near Portland's Back Cove
Terrace/patio

Sauna & fire table near Portland's Back Cove

10.0 out of 10, Exceptional, (3)
"Great location, clean property"
The price is CA $209
CA $472 total
includes taxes & fees
Sep 7 - Sep 8
Sauna & fire table near Portland's Back Cove
Orchid Harbor, Bailey Island 3BR
Interior

Orchid Harbor, Bailey Island 3BR

10.0 out of 10, Exceptional, (3)
"Orchid Harbor was perfect for my 3 week escape from life. Bailey Island is quiet and the house is comfortable and accommodating for family and friends.The outdoor seating along the ocean was our favorite place to be."
The price is CA $250
CA $607 total
includes taxes & fees
Sep 15 - Sep 16
Orchid Harbor, Bailey Island 3BR
30 Acres with Woodland Trails and Playground
Fridge, microwave, oven, stovetop

30 Acres with Woodland Trails and Playground

2.0 star property
10.0 out of 10, Exceptional, (1)
"Spent a week with my family at this lovely property in Freeport, ME. The location is ideal to visit various attractions nearby. Including the pinturesque dowtown. The house was clean and had everything needed to have a pleasant stay away from home. "
The price is CA $272
CA $809 total
includes taxes & fees
Sep 24 - Sep 25
30 Acres with Woodland Trails and Playground
Charming Studio apartment with WiFi, AC in welcoming Portland
Interior

Charming Studio apartment with WiFi, AC in welcoming Portland

9.6 out of 10, Exceptional, (5)
"This was a great stay through and through. Excellent condition, very responsive before and during the stay, and a great location. 10/10 will recommend to anyone staying in Portland! "
The price is CA $172
CA $315 total
includes taxes & fees
Sep 3 - Sep 4
Charming Studio apartment with WiFi, AC in welcoming Portland
THE LILLIPAD.Off-grid A frame. Sebago lake region!
Property grounds

THE LILLIPAD.Off-grid A frame. Sebago lake region!

10.0 out of 10, Exceptional, (2)
"Charming cabin. Well maintained. Loved my stay! Highly recommend."
The price is CA $208
CA $258 total
includes taxes & fees
Sep 9 - Sep 10
THE LILLIPAD.Off-grid A frame. Sebago lake region!
Studio Unit Walkable Everywhere
1 bedroom, bed sheets

Studio Unit Walkable Everywhere

8.0 out of 10, Very good, (2)
"Great, comfortable place to stay. The location is super walkable. There are several bars/restaurants very close, and other areas are close enlighten to walk to as well (I.e. Congress Street). Commercial is a bit of a walk, but if you’re like us and love to walk a new area. It’s not that far. The bed is comfortable and the place was very clean. Communication was great. We would stay here again!"
The price is CA $144
CA $244 total
includes taxes & fees
Sep 2 - Sep 3
Studio Unit Walkable Everywhere
Lakeview Central Hub
Microwave, oven, stovetop

Lakeview Central Hub

10.0 out of 10, Exceptional, (1)
"Beautiful place. Super quick communication. Quiet neighborhood. Loved it!"
The price is CA $229
CA $483 total
includes taxes & fees
Sep 2 - Sep 3
Lakeview Central Hub
Relaxing A-Frame with Hot Tub and Lake Access
Exterior

Relaxing A-Frame with Hot Tub and Lake Access

10.0 out of 10, Exceptional, (2)
"Great house, we had a wonderful time!"
The price is CA $323
CA $745 total
includes taxes & fees
Sep 2 - Sep 3
Relaxing A-Frame with Hot Tub and Lake Access
Coastal Escape | Hot Tub Fire Pit Chef Kitchen
Outdoor spa tub

Coastal Escape | Hot Tub Fire Pit Chef Kitchen

9.4 out of 10, Exceptional, (3)
"Really nice place. Beds are comfortable. Had nice hot tub with propane fire. Lovely back patio. "
The price is CA $480
CA $921 total
includes taxes & fees
Sep 7 - Sep 8
Coastal Escape | Hot Tub Fire Pit Chef Kitchen
Bird Watching Paradise @ Waterfront Harpswell with Private Deck
Private kitchen

Bird Watching Paradise @ Waterfront Harpswell with Private Deck

10.0 out of 10, Exceptional, (1)
"Super location, very private, responsive host, lovely, clean. Very lucky to have been able to stay here!"
The price is CA $412
CA $714 total
includes taxes & fees
Sep 2 - Sep 3
Bird Watching Paradise @ Waterfront Harpswell with Private Deck
Full sized home
Interior

Full sized home

9.8 out of 10, Exceptional, (37)
"The house was lovely. Very comfortable place. Within 15- 20 mins to a store or restaurants."
The price is CA $278
CA $497 total
includes taxes & fees
Sep 2 - Sep 3
Full sized home
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
Fridge, microwave, oven, stovetop

Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport

10.0 out of 10, Exceptional, (4)
"We had a wonderful time in Freeport, getting some Christmas season shopping in and bring our 4 year old to the Sparkle weekend festivities. "
The price is CA $397
CA $1,018 total
includes taxes & fees
Sep 28 - Sep 29
Beautiful Stay in Downtown Freeport, Beautiful Stay in Downtown Freeport
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
Sign in
Sign up, it's free

Top New Gloucester Hotel Reviews

Find out more about New Gloucester

Find out more about New Gloucester

New Gloucester Vacation Homes information

Number of reviews
Accommodation
637 Vacation Homes
Lowest Price
CA $158
Highest Price
CA $669

Explore a world of travel with Expedia

Explore a world of travel with Expedia